Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Recent Advances in Dimethyl Sulfoxide (DMSO) Used as a Multipurpose Reactant

Author(s): Su-Qian Cai, Ke-Feng Zhang* and Xiao-Hua Cai*

Volume 26, Issue 2, 2022

Published on: 12 January, 2022

Page: [91 - 121] Pages: 31

DOI: 10.2174/1385272826666220112162942

Price: $65

Abstract

Dimethyl sulfoxide (DMSO) is not only a common and cheap aprotic polar solvent with low toxicity but also serves as an efficient and multipurpose reactant, and has widely been used in organic synthesis. DMSO as an important precursor can effectively introduce a broad range of functional fragments into organic molecules, such as -Me, -CH, -CH2, -SMe2, - CH2SMe, -CH2SOMe, -SMe, -SO2Me, -SOMe or O substituents, and serves as a mild oxidant in organic transformations. Many significant achievements based on DMSO as a synthon in synthetic chemistry have rapidly been made over the past several years. To help researchers further understand the recent advances in the field, the review summarizes the applications of DMSO as carbon, sulfur, and oxygen sources and its use as the dual synthon in synthetic transformations.

Keywords: Dimethyl sulfoxide (DMSO), synthetic reagent, carbon source, sulfur source, oxygen source, dual synthon.

Graphical Abstract

[1]
(a) Vögtle, F.; Stoddart, J. F.; Shibasaki, M. Stimulating concepts in chemistry. Wiley-VCHWenheim, 2000.
(b) Nicolaou, K.C.; Hale, C.R.; Nilewski, C.; Ioannidou, H.A. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance. Chem. Soc. Rev., 2012, 41(15), 5185-5238.
[http://dx.doi.org/10.1039/c2cs35116a] [PMID: 22743704]
(c) Shi, M.; Lu, J-M.; Wei, Y.; Shao, L-X. Rapid generation of molecular complexity in the Lewis or brønsted acid-mediated reactions of methylenecyclopropanes. Acc. Chem. Res., 2012, 45(4), 641-652.
[http://dx.doi.org/10.1021/ar200237z] [PMID: 22166122]
[2]
Martin, D.; Weise, A.; Niclas, H.J. The solvent dimethyl sulfoxide. Angew. Chem. Int. Ed., 1967, 6(4), 318-334.
[http://dx.doi.org/10.1002/anie.196703181] [PMID: 4963226]
[3]
Soroko, I.; Bhole, Y.; Livingston, A.G. Environmentally friendly route for the preparation of solvent resistant polyimide nanofiltration membranes. Green Chem., 2011, 13, 162-168.
[http://dx.doi.org/10.1039/C0GC00155D]
[4]
(a) Wu, X.F.; Natte, K. The applications of dimethyl sulfoxide as reagent in organic synthesis. Adv. Synth. Catal., 2016, 358, 336-352.
[http://dx.doi.org/10.1002/adsc.201501007]
(b) Magolan, J.; Jones-Mensah, E.; Karki, M. Dimethyl sulfoxide as a synthon in organic chemistry. Synthesis, 2016, 48, 1421-1436.
[http://dx.doi.org/10.1055/s-0035-1560429]
[5]
(a) Chen, Y. Recent advances in methylation: A guide for selecting methylation reagents. Chemistry, 2019, 25(14), 3405-3439.
[http://dx.doi.org/10.1002/chem.201803642] [PMID: 30328642]
(b) Barreiro, E.J.; Kümmerle, A.E.; Fraga, C.A.M. The methylation effect in medicinal chemistry. Chem. Rev., 2011, 111(9), 5215-5246.
[http://dx.doi.org/10.1021/cr200060g] [PMID: 21631125]
(c) Schönherr, H.; Cernak, T. Profound methyl effects in drug discovery and a call for new C-H methylation reactions. Angew. Chem. Int. Ed. Engl., 2013, 52(47), 12256-12267.
[http://dx.doi.org/10.1002/anie.201303207] [PMID: 24151256]
(d) Ritchie, T.J.; Macdonald, S.J.F.; Pickett, S.D. Insights into the impact of N- and O-methylation on aqueous solubility and lipophilicity using matched molecular pair analysis. MedChemComm, 2015, 6, 1787-1797.
[http://dx.doi.org/10.1039/C5MD00309A]
(e) Kuntz, K.W.; Campbell, J.E.; Keilhack, H.; Pollock, R.M.; Knutson, S.K.; Porter-Scott, M.; Richon, V.M.; Sneeringer, C.J.; Wigle, T.J.; Allain, C.J.; Majer, C.R.; Moyer, M.P.; Copeland, R.A.; Chesworth, R. The importance of being me: Magic methyls, methyltransferase inhibitors, and the discovery of tazemetostat. J. Med. Chem., 2016, 59(4), 1556-1564.
[http://dx.doi.org/10.1021/acs.jmedchem.5b01501] [PMID: 26769278]
[6]
Atkinson, B.N.; Williams, J.M.J. Dimethylsulfoxide as an N-methylation reagent for amines and aromatic nitro compounds. ChemCatChem, 2014, 6, 1860-1862.
[http://dx.doi.org/10.1002/cctc.201400015]
[7]
Kawai, K.; Li, Y-S.; Song, M-F.; Kasai, H. DNA methylation by dimethyl sulfoxide and methionine sulfoxide triggered by hydroxyl radical and implications for epigenetic modifications. Bioorg. Med. Chem. Lett., 2010, 20(1), 260-265.
[http://dx.doi.org/10.1016/j.bmcl.2009.10.124] [PMID: 19914833]
[8]
Li, Z.J.; Cui, X.S.; Niu, L.; Ren, Yi.; Bian, M.H.; Yang, X.B.; Yang, B.; Yan, Q.Q.; Zhao, J.C. An iron (II) chloride-promoted radical cascade methylation or α-chloro-β-methylation of N-arylacrylamides with dimethyl sulfoxide. Adv. Synth. Catal., 2017, 359, 246-249.
[http://dx.doi.org/10.1002/adsc.201601001]
[9]
Zhang, R.; Shi, X.Q.; Yan, Q.Q.; Li, Z.J.; Wang, Z.; Yu, H.F.; Wang, X.K.; Qi, J.; Jiang, M.L. Free-radical initiated cascade methylation or trideuteromethylation of isocyanides with dimethyl sulfoxides. RSC Advances, 2017, 7, 38830-38833.
[http://dx.doi.org/10.1039/C7RA08484F]
[10]
Xie, Z.; Li, P.; Hu, Y.; Xu, N.; Wang, L. Visible-light-induced and iron-catalyzed methylation of N-arylacrylamides with dimethyl sulphoxide: a convenient access to 3-ethyl-3-methyl oxindoles. Org. Biomol. Chem., 2017, 15(19), 4205-4211.
[http://dx.doi.org/10.1039/C7OB00779E] [PMID: 28448075]
[11]
Jiang, S.; Yang, Z.; Guo, Z.; Li, Y.; Chen, L.; Zhu, Z.; Chen, X. Transition metal-free α-methylation of 1,8-naphthyridine derivatives using DMSO as methylation reagent. Org. Biomol. Chem., 2019, 17(31), 7416-7424.
[http://dx.doi.org/10.1039/C9OB01490J] [PMID: 31359026]
[12]
Yang, P.; Xu, W.; Wang, R.; Zhang, M.; Xie, C.; Zeng, X.; Wang, M. Potassium tert-butoxide-mediated condensation cascade reaction: transition metal-free synthesis of multisubstituted aryl indoles and benzofurans. Org. Lett., 2019, 21(10), 3658-3662.
[http://dx.doi.org/10.1021/acs.orglett.9b01093] [PMID: 31025566]
[13]
Jiang, X.; Wang, C.; Wei, Y.; Xue, D.; Liu, Z.; Xiao, J. A general method for N-methylation of amines and nitro compounds with dimethylsulfoxide. Chemistry, 2014, 20(1), 58-63.
[http://dx.doi.org/10.1002/chem.201303802] [PMID: 24327323]
[14]
Jia, J.; Jiang, Q.; Zhao, A.; Xu, B.; Liu, Q.; Luo, W-P.; Guo, C-C. Copper-catalyzed O-methylation of carboxylic acids using DMSO as a methyl source. Synthesis, 2016, 48, 421-428.
[http://dx.doi.org/10.1055/s-0035-1560967]
[15]
Wu, X.; Zhang, J.J.; Liu, S.; Gao, Q.H.; Wu, A.X. An efficient synthesis of polysubstituted pyridines via Csp3-H oxidation and C-S cleavage of dimethyl sulfoxide. Adv. Synth. Catal., 2016, 358, 218-225.
[http://dx.doi.org/10.1002/adsc.201500683]
[16]
Jadhav, S.D.; Singh, A. Oxidative annulations involving DMSO and formamide: K2S2O8 mediated syntheses of quinolines and pyrimidines. Org. Lett., 2017, 19(20), 5673-5676.
[http://dx.doi.org/10.1021/acs.orglett.7b02838] [PMID: 28980820]
[17]
Liu, Y.F.; Hu, Y.Q.; Cao, Z.Z.; Zhan, X.; Luo, W.P.; Liu, Q.; Guo, C.C. Copper-catalyzed aerobic oxidative cyclization of anilines, aryl methyl ketones and DMSO: Efficient assembly of 2-arylquinolines. Adv. Synth. Catal., 2018, 360, 2691-2695.
[http://dx.doi.org/10.1002/adsc.201800373]
[18]
Zheng, K.; Zhuang, S.; Shu, W.; Wu, Y.; Yang, C.; Wu, A. Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source. Chem. Commun. (Camb.), 2018, 54(84), 11897-11900.
[http://dx.doi.org/10.1039/C8CC06908E] [PMID: 30276382]
[19]
Lee, S.; Sim, J.; Jo, H.; Viji, M.; Srinu, L.; Lee, K.; Lee, H.; Manjunatha, V.; Jung, J-K. Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon. Org. Biomol. Chem., 2019, 17(35), 8067-8070.
[http://dx.doi.org/10.1039/C9OB01629E] [PMID: 31451812]
[20]
Kumar, P.; Kapur, M. Unusual reactivity of 4-vinyl isoxazoles in the copper-mediated synthesis of pyridines, employing DMSO as a one-carbon surrogate. Org. Lett., 2020, 22(15), 5855-5860.
[http://dx.doi.org/10.1021/acs.orglett.0c01935] [PMID: 32645267]
[21]
Zhu, X.; Zhang, F.; Kuang, D.; Deng, G.; Yang, Y.; Yu, J.; Liang, Y. 2S as sulfur source and DMSO as carbon source for the synthesis of 2-unsubstituted benzothiazoles. Org. Lett., 2020, 22(10), 3789-3793.
[http://dx.doi.org/10.1021/acs.orglett.0c00994] [PMID: 32362124]
[22]
Wakade, S.B.; Tiwari, D.K.; Phanindrudu, M.; Pushpendra Tiwari, D. K Synthesis of 3-keto-quinolines from enaminones, anilines and DMSO: Transition metal free one pot cascade. Tetrahedron, 2019, 75, 4024-4030.
[http://dx.doi.org/10.1016/j.tet.2019.06.030]
[23]
Hada, S.; Zai, M.S.K.; Roat, P.; Verma, V.P.; Shah, A.K.; Yadav, D.K.; Kumari, N. Metal-free graphene oxide promoted a novel multicomponent reaction for the synthesis of 3-substituted quinazolinones using DMSO as one carbon synthon. ChemistrySelect, 2019, 4, 1176-1179.
[http://dx.doi.org/10.1002/slct.201803623]
[24]
Liu, Y-F.; Ji, P-Y.; Xu, J-W.; Hu, Y-Q.; Liu, Q.; Luo, W-P.; Guo, C-C. Transition metal-free α-Csp3-H methylenation of ketones to form C=C bond using dimethyl sulfoxide as carbon source. J. Org. Chem., 2017, 82(14), 7159-7164.
[http://dx.doi.org/10.1021/acs.joc.7b00619] [PMID: 28650632]
[25]
Pan, X.J.; Liu, Q.; Chang, L.M.; Yuan, G.Q. Ammonium iodide-promoted cyclization of ketones with DMSO and ammonium acetate for synthesis of substituted pyridines. RSC Advances, 2015, 5, 51183-51187.
[http://dx.doi.org/10.1039/C5RA07584J]
[26]
Wang, F.Y.; Shen, J.H.; Cheng, G.L.; Cui, X.L. Practical access to 1,3,5-triarylbenzenes from chalcones and DMSO. RSC Advances, 2015, 5, 73180-73183.
[http://dx.doi.org/10.1039/C5RA13137E]
[27]
Chang, L.M.; Lai, J.Y.; Yuan, G.Q. One-pot synthesis of hantzsch pyridines via NH4I promoted condensation of 1,3-dicarbonyl compounds with DMSO and NH4OAc. Chin. J. Chem., 2016, 34, 887-894.
[http://dx.doi.org/10.1002/cjoc.201600255]
[28]
Xie, C.; Zhang, Z.; Li, D.; Gong, J.; Han, X.; Liu, X.; Ma, C. Dimethyl sulfoxide involved one-pot synthesis of quinoxaline derivatives. J. Org. Chem., 2017, 82(7), 3491-3499.
[http://dx.doi.org/10.1021/acs.joc.6b02977] [PMID: 28256123]
[29]
Yuan, J.; Yu, J-T.; Jiang, Y.; Cheng, J. Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines. Org. Biomol. Chem., 2017, 15(6), 1334-1337.
[http://dx.doi.org/10.1039/C6OB02714H] [PMID: 28106211]
[30]
Xu, X.; Yang, Y.; Zhang, X.; Yi, W. Direct synthesis of quinolines via Co(III)-catalyzed and DMSO involved C−H activation/cyclization of anilines with alkynes. Org. Lett., 2018, 20(3), 566-569.
[http://dx.doi.org/10.1021/acs.orglett.7b03673] [PMID: 29323496]
[31]
Xue, L.L.; Cheng, G.L.; Zhu, R.F.; Cui, X.L. Acid-promoted oxidative methylenation of 1,3-dicarbonyl compounds with DMSO: application to the three-component synthesis of Hantzsch-type pyridines. RSC Advances, 2017, 7, 44009-44012.
[http://dx.doi.org/10.1039/C7RA07442E]
[32]
Gao, Y.J.; Zhou, D.H.; Ma, Y.M. α-Csp3-H Methylenation of diketones to synthesize methylene-bridged bis-1,3-dicarbonyl compounds and polysubstituted pyridines using the DMSO/selectfluor system. ChemistrySelect, 2018, 3, 9374.
[http://dx.doi.org/10.1002/slct.201801996]
[33]
Moghaddam, F.M.; Tavakoli, G.; Saeednia, B. Ni-Catalyzed Synthesis of Methylenebisamides: Dual role of DMSO both as methylene source and oxidant. ChemistrySelect, 2017, 2, 1316-1322.
[http://dx.doi.org/10.1002/slct.201601639]
[34]
Ai, H-J.; Qi, X.X.; Peng, J-B.; Ying, J.; Wu, X-F. Palladium-catalyzed cross-coupling of arylboronic acid and benzonitriles with DMSO as the methylene source. Asian J. Org. Chem., 2018, 7(10), 2045-2048.
[http://dx.doi.org/10.1002/ajoc.201800502]
[35]
Talukdar, R. Dimethyl sulfoxide as a “methylene” source: Ru(II) photo-catalysedsynthesis of acetals from alcohols. New J. Chem., 2019, 43, 13334-13338.
[http://dx.doi.org/10.1039/C9NJ03422F]
[36]
Zhang, X.; Zhou, Z.; Xu, H.; Xu, X.; Yu, X.; Yi, W. Cobalt-catalyzed allylation of amides with styrenes using DMSO as both the solvent and the α-methylene source. Org. Lett., 2019, 21(18), 7248-7253.
[http://dx.doi.org/10.1021/acs.orglett.9b02462] [PMID: 31512879]
[37]
Zhang, Y.; Zhou, D.H.; Ma, Y.M.; Chen, J. DMSO-mediated synthesis of methylene-bridged unsymmetrical bisamides in the presence of AcOH. Synthesis, 2020, 52, 297-303.
[http://dx.doi.org/10.1055/s-0039-1690031]
[38]
Sun, K.; Wang, X.; Jiang, Y.; Lv, Y.; Zhang, L.; Xiao, B.; Li, D.; Zhu, Z.; Liu, L. Direct N-methylation reaction using DMSO as one-carbon bridge: convenient access to heterocycle-containing β-amino ketones. Chem. Asian J., 2015, 10(3), 536-539.
[http://dx.doi.org/10.1002/asia.201403358] [PMID: 25581899]
[39]
Sun, K.; Lv, Y.H.; Zhu, Z.H.; Zhang, L.P.; Wu, H.K.; Liu, L.; Jiang, Y.Q.; Xiao, B.B.; Wang, X. Oxidative C–S bond cleavage reaction of DMSO for C–N and C–C bond formation: new mannich-type reaction for β-amino ketones. RSC Advances, 2015, 5, 3094-3097.
[http://dx.doi.org/10.1039/C4RA14249G]
[40]
Liu, P.; Shen, Z.; Yuan, Y.; Sun, P. Synthesis of symmetrical methylene-bridged imidazoheterocycles using DMSO as methylene source under metal-free conditions. Org. Biomol. Chem., 2016, 14(27), 6523-6530.
[http://dx.doi.org/10.1039/C6OB00977H] [PMID: 27298191]
[41]
Garza-Sanchez, R.A.; Patra, T.; Tlahuext-Aca, A.; Strieth-Kalthoff, F.; Glorius, F. DMSO as a switchable alkylating agent in heteroarene C-H functionalization. Chemistry, 2018, 24, 10064-10068.
[http://dx.doi.org/10.1002/chem.201802352] [PMID: 29750378]
[42]
Cao, H.; Lei, S.; Li, N.; Chen, L.; Liu, J.; Cai, H.; Qiu, S.; Tan, J. Cu-catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen. Chem. Commun. (Camb.), 2015, 51(10), 1823-1825.
[http://dx.doi.org/10.1039/C4CC09134E] [PMID: 25519843]
[43]
Ni, Y.; Zuo, H.; Yu, H.; Wu, Y.; Zhong, F. Synergistic catalysis-enabled thia-aza-prins cyclization with DMSO and disulfides: entry to sulfenylated 1,3-oxazinanes and oxazolidines. Org. Lett., 2018, 20(18), 5899-5904.
[http://dx.doi.org/10.1021/acs.orglett.8b02551] [PMID: 30199259]
[44]
Cao, Z.; Shi, D.; Qu, Y.; Tao, C.; Liu, W.; Yao, G. Synthesis of dimethyl aryl acylsulfonium bromides from aryl methyl ketones in a DMSO-HBr system. Molecules, 2013, 18(12), 15717-15723.
[http://dx.doi.org/10.3390/molecules181215717] [PMID: 24352024]
[45]
Shen, T.; Huang, X.; Liang, Y.F.; Jiao, N. Cu-Catalyzed transformation of alkynes and alkenes with azide and dimethyl sulfoxide reagents. Org. Lett., 2015, 17(24), 6186-6189.
[http://dx.doi.org/10.1021/acs.orglett.5b03179] [PMID: 26646089]
[46]
Zhang, C.X.; Zheng, L.; Yan, Q.; Hu, Q.Q.; Jia, F.C.; Chen, Y.F. A direct P2O5-mediated synthesis of diverse sulfur-containing triazoles via alkylation of NH-1,2,3-triazoles with dimethyl sulfoxide. ChemistrySelect, 2018, 3, 10277-10280.
[http://dx.doi.org/10.1002/slct.201802875]
[47]
Phanindrudu, M.; Tiwari, D.K.; Aravilli, V.K.; Bhardwaj, K.C.; Sabapathi, G.; Likhar, P.R.; Tiwari, D.K. Magnetically recoverable Cu0/Fe3O4-catalysed one-pot tandem synthesis of sulfur-containing triazoles from alkynes and azide: DMSO acts as an alkylating agent. Eur. J. Org. Chem., 2016, 27, 4629-4634.
[http://dx.doi.org/10.1002/ejoc.201600740]
[48]
Lu, M.; Qin, H.; Lin, Z.; Huang, M.; Weng, W.; Cai, S. Visible-light-enabled oxidative alkylation of unactivated alkenes with dimethyl sulfoxide through concomitant 1,2-aryl migration. Org. Lett., 2018, 20(23), 7611-7615.
[http://dx.doi.org/10.1021/acs.orglett.8b03340] [PMID: 30485102]
[49]
Chougala, B.M.; Samundeeswari, S.; Holiyachi, M.; Naik, N.S.; Shastri, L.A.; Sunagar, V.A. An efficient and catalyst free methylthiolation of 4-(bromomethyl)-2H-chromen-2-ones with DMSO. Phosphorus Sulfur Silicon Relat. Elem., 2017, 192, 874-879.
[http://dx.doi.org/10.1080/10426507.2017.1290628]
[50]
Yu, S.T.; Liu, Y.W.; Wang, J.Z.; Luo, F.; Cheng, H.L.; Jiang, Y.B. 1,2,3-Triazole N(2)-chelated C–S coupling: Access to ortho methylthiolated 1,2,3-triazoles. Synth. Commun., 2018, 48, 2566-2574.
[http://dx.doi.org/10.1080/00397911.2018.1514050]
[51]
Hu, L.; Wang, D.; Chen, X.; Yu, L.; Yu, Y.; Tan, Z.; Zhu, G. Copper-catalyzed decarboxylative methylthiolation of aromatic carboxylate salts with DMSO. Org. Biomol. Chem., 2017, 15(27), 5674-5679.
[http://dx.doi.org/10.1039/C7OB01315A] [PMID: 28654110]
[52]
Ravi, C.; Chandra Mohan, D.; Adimurthy, S. Dual role of p-tosylchloride: copper-catalyzed sulfenylation and metal free methylthiolation of imidazo[1,2-a]pyridines. Org. Biomol. Chem., 2016, 14(7), 2282-2290.
[http://dx.doi.org/10.1039/C5OB02475G] [PMID: 26795550]
[53]
Hu, L.; Chen, X.; Yu, L.; Yu, Y.Q.; Tana, Z.; Zhu, G.G.; Gui, Q.W. Highly mono-selective orth-methylthiolation of benzamides via cobalt-catalyzed sp2 C-H activation. Org. Chem. Front., 2018, 5, 216-221.
[http://dx.doi.org/10.1039/C7QO00717E]
[54]
Wang, M.; Tang, B-C.; Ma, J-T.; Wang, Z-X.; Xiang, J-C.; Wu, Y-D.; Wang, J.G.; Wu, A.X. I2/DMSO-mediated multicomponent reaction of o-hydroxyaryl methyl ketones, rongalite, and DMSO: access to C3-sulfenylated chromones. Org. Biomol. Chem., 2019, 17(6), 1535-1541.
[http://dx.doi.org/10.1039/C8OB02994F] [PMID: 30681108]
[55]
Rajasekar, S.; Krishna, T.P.A.; Tharmalingam, N.; Andivelu, I.; Mylonakis, E. Metal-free C-H thiomethylation of quinones using iodine and DMSO and study of antibacterial activity. ChemistrySelect, 2019, 4, 2281-2287.
[http://dx.doi.org/10.1002/slct.201803816]
[56]
Tong, H.Q.; Chen, C.; Liu, W.B.; Pan, Y.P.; Duan, L.H. Chlorothiomethylation of alkynes with HCl and dimethyl sulfoxide: An efficient approach to (E)-α-chloro-β-(methylthio)alkenes. Asian J. Org. Chem., 2019, 4, 479-481.
[http://dx.doi.org/10.1002/ajoc.201900108]
[57]
Hazarika, H.; Neog, K.; Sharma, A.; Das, B.; Gogoi, P. Three-component coupling reactions of aryne, DMSO, and activated alkyne: Stereoselective synthesis of 2-[(o-methylthio)aryloxy]-substituted dialkyl maleates. J. Org. Chem., 2019, 84(9), 5846-5854.
[http://dx.doi.org/10.1021/acs.joc.9b00090] [PMID: 30943034]
[58]
An, Z.Y.; She, Y.; Yang, X.D.; Pang, X.B.; Yan, R.L. Metal-free synthesis 3-methylthiofurans from homopropargylic alcohols and DMSO via tandem sulfenylation/cyclization reaction in one-pot manner. Org. Chem. Front., 2016, 3, 1746-1749.
[http://dx.doi.org/10.1039/C6QO00462H]
[59]
Rather, S.A.; Kumar, A.; Ahmed, Q.N. Iodine-DMSO-promoted divergent reactivities of arylacetylenes. Chem. Commun. (Camb.), 2019, 55(31), 4511-4514.
[http://dx.doi.org/10.1039/C9CC00346K] [PMID: 30919853]
[60]
An, X.C.; Zhang, B.B.; Li, X.X.; Du, T.S.; Ai, Z.K.; Zhang, C.L.; Xu, J.; Sun, F.X.; Zhang, Y.Ll.; Du, Y. F Construction of 4-(methylthio)isochromenones skeleton through regioselective intramolecular cyclization of 2-alkynylbenzoate mediated by DMSO/[D6]DMSO and SOCl2. Eur. J. Org. Chem., 2020, 852-859.
[http://dx.doi.org/10.1002/ejoc.201901723]
[61]
Chen, Z.K.; Cao, G.J.; Zhang, F.J.; Li, H.L.; Xu, J.F.; Miao, M.Z.; Ren, H.J. Metal-free mediated C-3 methylsulfanylation of imidazo[1,2-a]-pyridines with dimethyl sulfoxide as a methylsulfanylating agent. Synlett, 2017, 1795-1800.
[http://dx.doi.org/10.1055/s-0036-1588419]
[62]
Cui, X.F.; Liu, X.X.; Wang, X.J.; Tian, W.F.; Wei, D.D.; Huang, G.S. Copper-catalyzed ortho-thiomethylation of benzamides via 8-aminoquinoline-assisted C-H activation with dimethyl sulfoxide. ChemistrySelect, 2017, 2, 8607-8611.
[http://dx.doi.org/10.1002/slct.201702046]
[63]
Xiao, Y.; Wang, S.; Liu, J.Y.; Zhang, H.; Xu, Y.N. Copper(II) mediated C-H methylthiolation of 2-phenyl pyridines with dimethyl sulfoxide using an amino acid ligand. Tetrahedron Lett., 2019, 60, 1317-1320.
[http://dx.doi.org/10.1016/j.tetlet.2019.03.067]
[64]
Li, J.L.; Liu, G.L.; Shi, L.J.; Xing, Q.; Li, F.W. Cobalt modified N-doped carbon nanotubes for catalytic C=C bond formation via dehydrogenative coupling of benzyl alcohols and DMSO. Green Chem., 2017, 19, 5782-5788.
[http://dx.doi.org/10.1039/C7GC02335A]
[65]
Cao, C.C.; Zhang, L.; Zhou, G.; Dan, W.Y.; Wang, X.R.; Zhao, X.M. Application of DMSO in the synthesis of 1,4-disubstituted (but-1-en-3-ynyl)methylthioethers. ChemistrySelect, 2017, 2, 2985-2988.
[http://dx.doi.org/10.1002/slct.201700378]
[66]
Ghosh, K.; Ranjit, S.; Mal, D. A convenient method for the synthesis of aryl methyl sulfides via Cu(I)-mediated methylthiolation of haloarenes with DMSO. Tetrahedron Lett., 2015, 56, 5199-5202.
[http://dx.doi.org/10.1016/j.tetlet.2015.07.047]
[67]
Gao, X.; Pan, X.; Gao, J.; Jiang, H.; Yuan, G.; Li, Y. NH4I-mediated three-component coupling reaction: metal-free synthesis of β-alkoxy methyl sulfides from DMSO, alcohols, and styrenes. Org. Lett., 2015, 17(4), 1038-1041.
[http://dx.doi.org/10.1021/acs.orglett.5b00170] [PMID: 25671345]
[68]
Shukla, G.; Srivastava, A.; Nagaraju, A.; Raghuvanshi, K.; Singh, M.S. Iodine-mediated copper-catalyzed efficient α-C(sp2)-thiomethylation of α-oxoketene dithioacetals with dimethyl sulfoxide in one pot. Adv. Synth. Catal., 2015, 357, 3969-3976.
[http://dx.doi.org/10.1002/adsc.201500634]
[69]
Zou, J-F.; Huang, W-S.; Li, L.; Xu, Z.; Zheng, Z-J.; Yang, K-F.; Xu, L-W. DMSO as oxidant and sulfenylating agent for metal-free oxidation and methylthiolation of alcohol containing indoles. RSC Advances, 2015, 5, 30389-30393.
[http://dx.doi.org/10.1039/C5RA03606B]
[70]
Sharma, P.; Rohilla, S.; Jain, N. Copper acetate-DMSO promoted methylthiolation of arenes and heteroarenes. J. Org. Chem., 2015, 80(8), 4116-4122.
[http://dx.doi.org/10.1021/acs.joc.5b00443] [PMID: 25791785]
[71]
Gao, X.; Pan, X.; Gao, J.; Huang, H.; Yuan, G.; Li, Y. Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones. Chem. Commun. (Camb.), 2015, 51(1), 210-212.
[http://dx.doi.org/10.1039/C4CC07606K] [PMID: 25406694]
[72]
Zhang, J.; Cheng, S.; Cai, Z.; Liu, P.; Sun, P. Radical addition cascade cyclization of 1,6-enynes with DMSO to access methylsulfonylated and carbonylated benzofurans under transition-metal-free conditions. J. Org. Chem., 2018, 83(16), 9344-9352.
[http://dx.doi.org/10.1021/acs.joc.8b01265] [PMID: 29969266]
[73]
Pramanik, M.M.D.; Rastogi, N. Visible light catalyzed methylsulfoxidation of (het)aryl diazonium salts using DMSO. Chem. Commun. (Camb.), 2016, 52(55), 8557-8560.
[http://dx.doi.org/10.1039/C6CC04142F] [PMID: 27321904]
[74]
Dai, P.; Luo, K.; Yu, X.; Yang, W-C.; Wu, L.; Zhang, W-H. Tert-butyl nitrite mediated expeditious methylsulfoxidation of tetrazole-amines with DMSO: Metal-free synthesis of antifungal active methylsulfinyl-1H-tetrazole derivatives. Adv. Synth. Catal., 2018, 360, 468-473.
[http://dx.doi.org/10.1002/adsc.201701364]
[75]
Fu, D.; Dong, J.; Du, H.; Xu, J. Methanesulfinylation of benzyl halides with dimethyl sulfoxide. J. Org. Chem., 2020, 85(4), 2752-2758.
[http://dx.doi.org/10.1021/acs.joc.9b03041] [PMID: 31873024]
[76]
Zhao, P.; Wu, X.; Geng, X.; Wang, C.; Zhou, Y.; Wu, Y-D.; Wu, A-X.I. 2/PhI(OAc)2 copromoted amination reaction: Synthesis of α-dicarbonylsulfoximine derivatives by incorporating an intact dimethyl sulfoxide. J. Org. Chem., 2019, 84(12), 8322-8329.
[http://dx.doi.org/10.1021/acs.joc.9b01160] [PMID: 31140280]
[77]
Liang, Y-F.; Wu, K.; Song, S.; Li, X.; Huang, X.; Jiao, N. I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide. Org. Lett., 2015, 17(4), 876-879.
[http://dx.doi.org/10.1021/ol5037387] [PMID: 25650782]
[78]
Mupparapu, N.; Vishwakarma, R.A.; Ahmed, Q.N. Iodine-DMSO promoted/C-H (SP3) functionalization approach to α-ketoamides. Tetrahedron, 2015, 71, 3417-3421.
[http://dx.doi.org/10.1016/j.tet.2015.03.088]
[79]
Tamuli, K.J.; Bordoloi, M.K.I-I. 2-DMSO: An improved microwave-assisted selective oxidation of alkenes into 1,2-diketones. ChemistrySelect, 2018, 3, 7513-7517.
[http://dx.doi.org/10.1002/slct.201800433]
[80]
Lu, Y.; Luo, M-J.; Hu, M.; Li, Y.; Li, J-H. Dimethyl sulfoxide as an oxygen atom source enabled tandem conversion of 2-alkynyl carbonyls to 1,2-dicarbonyls. Adv. Synth. Catal., 2020, 362, 1846-1850.
[http://dx.doi.org/10.1002/adsc.202000066]
[81]
Naidoo, S.; Jeena, V. Molecular iodine/DMSO mediated oxidation of internal alkynes and primary alcohols using a one-pot, two step approach towards 2,4,5-trisubstituted imidazoles: Substrate scope and mechanistic studies. Tetrahedron, 2020, 76131028
[http://dx.doi.org/10.1016/j.tet.2020.131028]
[82]
Prasad, P.K.; Reddi, R.N.; Sudalai, A. Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide−dimethyl sulfoxide combination: A facile synthesis of α-amino-ketones and esters. Org. Lett., 2016, 18(3), 500-503.
[http://dx.doi.org/10.1021/acs.orglett.5b03540] [PMID: 26800214]
[83]
Gujjarappa, R.; Vodnala, N.; Putta, V.P.R.K.; Reddy, V.G.; Malakar, C.C. Conversion of alkynes into 1,2-diketones using HFIP as sacrificial hydrogen donor and DMSO as dihydroxylating agent. Tetrahedron Lett., 2020, 61151588
[84]
Zhang, X.H.; Li, S-S.; Wang, L.; Xu, L.B.; Xiao, J.; Li, Z-J. 2-Methylquinoline promoted oxidative ring-opening of N-sulfonyl aziridines with DMSO: Facile synthesis of α-amino aryl ketones. Tetrahedron, 2016, 72, 8073-8077.
[http://dx.doi.org/10.1016/j.tet.2016.10.041]
[85]
Zha, G-F.; Fang, W-Y.; Leng, J.; Qin, H-L. A simple, mild and general oxidation of alcohols to aldehydes or ketones by SO2F2/K2CO3 using DMSO as solvent and oxidant. Adv. Synth. Catal., 2019, 361(10), 2262-2267.
[http://dx.doi.org/10.1002/adsc.201900104]
[86]
Xia, Z-H.; Gao, Z-H.; Dai, L.; Ye, S. Visible-light-promoted oxo-difluoroalkylation of alkenes with DMSO as the oxidant. J. Org. Chem., 2019, 84(11), 7388-7394.
[http://dx.doi.org/10.1021/acs.joc.9b01077] [PMID: 31083945]
[87]
Luo, X.; Fan, Z.; Zhang, B.; Chen, C.; Xi, C. Visible-light-triggered direct keto-difluoroacetylation of styrenes with (fluorosulfonyl)difluoroacetate and dimethyl sulfoxide leads to α-difluoroacetylated ketones. Chem. Commun. (Camb.), 2019, 55(73), 10980-10983.
[http://dx.doi.org/10.1039/C9CC06037E] [PMID: 31453610]
[88]
Shen, W-G.; Wu, Q-Y.; Gong, X-Y.; Ao, G-Z.; Liu, F. A facile method for hydroxytrifluoromethylation of alkenes with langlois reagent and DMSO. green chem., 2019, 21, 2983-2987.
[http://dx.doi.org/10.1039/C9GC00886A]
[89]
Li, L.; Luo, H.; Zhao, Z.; Li, Y.; Zhou, Q.; Xu, J.; Li, J.; Ma, Y-N. Photoredox-catalyzed remote difunctionalizations of alkenes to synthesize fluoroalkyl ketones with dimethyl sulfoxide as the oxidant. Org. Lett., 2019, 21(22), 9228-9231.
[http://dx.doi.org/10.1021/acs.orglett.9b03594] [PMID: 31680529]
[90]
Cao, Z.Z.; Lv, H.F.; Liu, Y.F.; Nie, Z.W.; Liu, H.P.; Yang, T.L.; Luo, W.P.; Liu, Q.; Guo, C.C. Dimethyl sulfoxide oxygen donor-based annulation of ketones and ammonium persulfate: Regioselective synthesis of 2,4-disubstituted oxazoles. Adv. Synth. Catal., 2019, 361, 1632-1640.
[http://dx.doi.org/10.1002/adsc.201801671]
[91]
Liu, H.; Liu, J.; Cheng, X.; Jia, X.; Yu, L.; Xu, Q. DMSO-triggered complete oxygen transfer leading to accelerated aqueous hydrolysis of organohalides under mild conditions. ChemSusChem, 2019, 12(13), 2994-2998.
[http://dx.doi.org/10.1002/cssc.201802138] [PMID: 30511457]
[92]
Venkateswarlu, V.; Aravinda Kumar, K.A.; Gupta, S.; Singh, D.; Vishwakarma, R.A.; Sawant, S.D. DMSO/I2 mediated C-C bond cleavage of α-ketoaldehydes followed by C-O bond formation: A metal-free approach for one-pot esterification. Org. Biomol. Chem., 2015, 13(29), 7973-7978.
[http://dx.doi.org/10.1039/C5OB01015B] [PMID: 26110656]
[93]
Li, H-L. An, Xing-Lan; Ge, Li-Shi; Luo, Xiaoyan; Deng, Wei-Ping Catalytic α-hydroxylation of ketones under CuBr2 or HBr/DMSO systems. Tetrahedron, 2015, 71, 3247-3252.
[http://dx.doi.org/10.1016/j.tet.2015.03.116]
[94]
Salvanna, N.; Reddy, L.M.; Kumar, R.A.; Das, B. Unactivated sp3 C-H functionalization by I2/DMSO: An efficient method to synthesize isatins. ChemistrySelect, 2018, 3, 8019-8022.
[http://dx.doi.org/10.1002/slct.201801176]
[95]
Jayram, J.; Xulu, B.A.; Jeena, V. Iodine/DMSO promoted oxidation of benzylic Csp3-H bonds to diketones -a mechanistic investigation. Tetrahedron, 2019, 75130617
[http://dx.doi.org/10.1016/j.tet.2019.130617]
[96]
Song, S.; Huang, X.Q.; Liang, Y-F.; Tang, C.H.; Li, X.W.; Jiao, N. From simple organobromides or olefins to highly value-added bromohydrins: A versatile performance of dimethyl sulfoxide. Green Chem., 2015, 17, 2727-2731.
[http://dx.doi.org/10.1039/C5GC00184F]
[97]
Chebolu, R.; Bahuguna, A.; Sharma, R.; Mishra, V.K.; Ravikumar, P.C. An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: A new facet to classical DMSO oxidation. Chem. Commun. (Camb.), 2015, 51(84), 15438-15441.
[http://dx.doi.org/10.1039/C5CC05713B] [PMID: 26343873]
[98]
Dong, J.; Xu, J.X. NBS/DMSO-mediated synthesis of (2,3-dihydrobenzo[b][1,4] oxathiin-3-yl)methanols from aryloxymethylthiiranes. New J. Chem., 2018, 42, 9037-9044.
[http://dx.doi.org/10.1039/C8NJ01117F]
[99]
Wen, Z-K.; Liu, X-H.; Liu, Y-F.; Chao, J-B. Acid promoted direct cross-coupling of methyl ketones with dimethyl sulfoxide: Access to ketoallyl methylsulfides and –sulfones. Org. Lett., 2017, 19(21), 5798-5801.
[http://dx.doi.org/10.1021/acs.orglett.7b02753] [PMID: 29048901]
[100]
Zhu, X.M.; Li, W.G.; Luo, X.A.; Deng, G.B.; Liang, Y.; Liu, J.B. Catalyst-free and additive-free method for the synthesis of benzothiazolethiones from o-iodoanilines, DMSO and potassium sulfide. Green Chem., 2018, 20, 1970-1974.
[http://dx.doi.org/10.1039/C8GC00477C]
[101]
Xu, N.; Zhang, Y.; Chen, W.; Li, P.H.; Wang, L. Photoinduced N-methylation and N-sulfonylation of azobenzenes with DMSO under mild reaction conditions. Adv. Synth. Catal., 2018, 360, 1199-1208.
[http://dx.doi.org/10.1002/adsc.201701548]
[102]
Xu, C.; Jiang, S-F.; Wen, X-H.; Zhang, Q.; Zhou, Z-W.; Wu, Y-D.; Jia, F-C.; Wu, A-X. Dimethyl sulfoxide serves as a dual synthon: construction of 5-methyl pyrimidine derivatives via four component oxidative annulation. Adv. Synth. Catal., 2018, 360, 2267-2271.
[http://dx.doi.org/10.1002/adsc.201800180]
[103]
Liu, Y.F.; Hu, Y.Q.; Cao, Z.Z.; Zhan, X.; Luo, W.P.; Liu, Q.; Guo, C.C. Direct assembly of polysubstituted furans via C(sp3)–H bond functionalization by using dimethyl sulfoxide as a dual synthon. Adv. Synth. Catal., 2019, 361, 1084-1091.
[http://dx.doi.org/10.1002/adsc.201801429]
[104]
Hua, J.W.; Xu, J.Q.; Xu, J.; Zhou, B.C.; Zhang, D.; Yang, Z.; Fang, Z.; Guo, K. Oxidative thioesterification of alkenes mediated by 1,3-dibromo-5,5-dimethylhydantoin and DMSO for the synthesis of α-ketothioesters. Eur. J. Org. Chem., 2019, 4056-4060.
[http://dx.doi.org/10.1002/ejoc.201900585]
[105]
Xu, X.F.; Zhou, Z.; Wang, Z.P.; Ma, X.N.; Chen, X.; Zhang, X.; Yu, X.Y.; Yi, W. Cobalt(III)-catalyzed and dimethyl sulfoxide-involved cross-coupling of ketones and amides for direct synthesis of β-amino ketones. Adv. Synth. Catal., 2019, 361, 4278-4285.
[http://dx.doi.org/10.1002/adsc.201900717]
[106]
Hazarika, H.; Gogoi, P. Direct synthesis of ortho-methylthio allyl and vinyl ethers via three component reaction of aryne, activated alkene and DMSO. Org. Biomol. Chem., 2020, 18(14), 2727-2738.
[http://dx.doi.org/10.1039/D0OB00275E] [PMID: 32219226]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy