Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Letter Article

Friedel-Crafts Benzylation of Unprotected Anilines with Indole-3- carbinols to Access Trifluoro-methyl(indolyl)phenylmethanes

Author(s): Paidamoyo Chigumbu, Junfeng Fu, Ingrid Rakielle Tsapy Takia, Yongjiang Wang* and Xiaoyu Han*

Volume 19, Issue 5, 2022

Published on: 25 February, 2021

Page: [353 - 361] Pages: 9

DOI: 10.2174/1570178618666210225114226

Price: $65

Abstract

An unprecedented protocol for the efficient and highly chemoselective alkylation of unprotected anilines with deactivated CF3-indole-3-carbinols promoted by In(OTf)3 has been developed. A series of diversified trifluoromethylated (indolyl)phenylmethanes were produced featuring the C-alkylation in moderate to high chemical yields and with high regioselectivities.

Keywords: Lewis-acid, unprotected aniline, deactivated alcohol, Friedel-Crafts reaction, C-alkylation, fluorinated indole derivatives.

« Previous Next »
Graphical Abstract

[1]
(a) Böhm, H.J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem, 2004, 5(5), 637-643.
[http://dx.doi.org/10.1002/cbic.200301023] [PMID: 15122635]
(b) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceña, J.L.; Soloshonok, V.A.; Izawa, K.; Liu, H. Chem. Rev., 2016, 116(2), 422-518.
[http://dx.doi.org/10.1021/acs.chemrev.5b00392] [PMID: 26756377]
(c) Chem. Soc. Rev., 2008, 37(2), 308-319.
[PMID: 18197347]
(d) Gladysz, J.A.; Jurisch, M. Top. Curr. Chem., 2012, 308, 1-23.
[PMID: 21972027]
(e) Law, C-K.E.; Horváth, I.T. Org. Chem. Front., 2016, 3(8), 1048-1062.
[http://dx.doi.org/ 10.1039/C6QO00115G]
[2]
(a) Kirk, K.L. J. Fluor. Chem., 2006, 127(8), 1013-1029.
[http://dx.doi.org/10.1016/j.jfluchem.2006.06.007]
(b) Ojima, I. J. Fluor. Chem., 2017, 198, 10-23.
[http://dx.doi.org/10.1016/j.jfluchem.2016.12.016] [PMID: 28824201]
(c) Purser, S.; Moore, P.R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev., 2008, 37(2), 320-330.
[http://dx.doi.org/10.1039/B610213C] [PMID: 18197348]
(d) Shah, P.; Westwell, A.D.J. Inhib. Med. Chem., 2007, 22(5), 527-540.
[http://dx.doi.org/10.1080/14756360701425014]
(e) Pillaiyar, T.; Sedaghati, M.; Schnakenburg, G. Beilstein J. Org. Chem., 2020, 16, 778-790.
[http://dx.doi.org/10.3762/bjoc.16.71] [PMID: 32395181]
[3]
(a) Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E. Hulliger. J. Chem. Soc. Rev., 2011, 40(7), 3496-3508.
[http://dx.doi.org/10.1039/c0cs00221f] [PMID: 21448484]
(b) Gillis, E.P.; Eastman, K.J.; Hill, M.D.; Donnelly, D.J.; Meanwell, N.A. J. Med. Chem., 2015, 58(21), 8315-8359.
[http://dx.doi.org/10.1021/acs.jmedchem.5b00258] [PMID: 26200936]
(c) Ismail, F.M.D. J. Fluor. Chem., 2002, 118(1-2), 27-33.
[http://dx.doi.org/10.1016/S0022-1139(02)00201-4]
(d) Corbett, J.W.; Ko, S.S.; Rodgers, J.D.; Gearhart, L.A.; Magnus, N.A.; Bacheler, L.T.; Diamond, S.; Jeffrey, S.; Klabe, R.M.; Cordova, B.C.; Garber, S.; Logue, K.; Trainor, G.L.; Anderson, P.S.; Erickson-Viitanen, S.K. J. Med. Chem., 2000, 43(10), 2019-2030.
[http://dx.doi.org/10.1021/jm990580e] [PMID: 10821714]
(e) Li, W.; Yan, Y.; Chang, Y.; Ding, L.; Liu, H.; You, Q. Med. Chem. Res., 2019, 28, 1783-1795.
[http://dx.doi.org/10.1007/s00044-019-02415-4]
[4]
(a) Liang, T.; Neumann, C.N.; Ritter, T. Angew. Chem., 2013, 125(32), 8372-8423.
[http://dx.doi.org/10.1002/ange.201206566]
(b) Chu, L.; Qing, F-L. Acc. Chem. Res., 2014, 47(5), 1513-1522.
[http://dx.doi.org/10.1021/ar4003202] [PMID: 24773518]
(c) Kelly, C.B.; Mercadante, M.A.; Leadbeater, N.E. Chem. Commun. Camb., 2013, 49(95), 11133-11148.
[http://dx.doi.org/10.1039/c3cc46266h] [PMID: 24162741]
(d) Haranahalli, K.; Honda, T.; Ojima, I. J. Fluor. Chem., 2019, 217, 29-40.
[http://dx.doi.org/10.1016/j.jfluchem.2018.11.002] [PMID: 31537946]
[5]
(a) Rueping, M.; Kuenkel, A.; Atodiresei, I. Chem. Soc. Rev., 2011, 40(9), 4539-4549.
[http://dx.doi.org/10.1039/c1cs15087a] [PMID: 21614342]
(b) You, S-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev., 2009, 38(8), 2190-2201.
[http://dx.doi.org/10.1039/b817310a] [PMID: 19623343]
(c) Zamfir, A.; Schenker, S.; Freund, M.; Tsogoeva, S.B. Org. Biomol. Chem., 2010, 8(23), 5262-5276.
[http://dx.doi.org/10.1039/c0ob00209g] [PMID: 20820680]
(d) Heravi, M.M.; Zadsirjan, V.; Saedi, P.; Momeni, T. RSC Advances, 2018, 8(70), 40061-40063.
[http://dx.doi.org/10.1039/C8RA07325B]
(e) Wang, X.; Liu, J.; Xu, L.; Hao, Z.; Wang, L.; Xiao, J. RSC Advances, 2015, 5(123), 101713-101717.
[http://dx.doi.org/10.1039/C5RA21919A]
(f) Cotos, L.; Donzel, M.; Elhabiri, M.; Davioud-Charvet, E. Chemistry, 2020, 26(15), 3314-3325.
[http://dx.doi.org/10.1002/chem.201904220] [PMID: 31746499]
(g) An, D.; Miao, X.; Ling, X.; Chen, X.; Rao, W. Adv. Synth. Catal. 2020.
[http://dx.doi.org/10.1002/adsc.202000020]
(h) Chen, L.; Xiao, B-X.; Du, W.; Chen, Y-C. Org. Lett., 2019, 21(14), 5733-5736.
[http://dx.doi.org/10.1021/acs.orglett.9b02108] [PMID: 31264878]
(i) Ramana, D.V.; Kumar, K.S.; Srujana, E.; Chandrasekharam, M. Eur. J. Org. Chem., 2019, 2019, 742-745.
[http://dx.doi.org/10.1002/ejoc.201801369]
(j) Salem, Z.M.; Saway, J.; Badillo, J.J. Org. Lett., 2019, 21(21), 8528-8532.
[http://dx.doi.org/10.1021/acs.orglett.9b02841] [PMID: 31638823]
[6]
(a) Palmieri, A.; Petrini, M.; Shaikh, R.R. Org. Biomol. Chem., 2010, 8(6), 1259-1270.
[http://dx.doi.org/10.1039/B919891A] [PMID: 20204191]
(b) Sun, F-L.; Zeng, M.; Gu, Q.; You, S.L. Chemistry, 2009, 15(35), 8709-8712.
[http://dx.doi.org/10.1002/chem.200901369] [PMID: 19644985]
(c) Kumar, R.; Van der Eycken, E.V. Chem. Soc. Rev., 2013, 42(3), 1121-1146.
[http://dx.doi.org/10.1039/C2CS35397K] [PMID: 23192192]
(d) Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev., 2012, 41(12), 4467-4483.
[http://dx.doi.org/10.1039/c2cs35024f] [PMID: 22576362]
[7]
(a) Bandini, M.; Tragni, M. Org. Biomol. Chem., 2009, 7(8), 1501-1507.
[http://dx.doi.org/10.1039/b823217b] [PMID: 19343234]
(b) Poulsen, T.B.; Jørgensen, K.A. Chem. Rev., 2008, 108(8), 2903-2915.
[http://dx.doi.org/10.1021/cr078372e] [PMID: 18500844]
[8]
(a) Vuković, V.D.; Richmond, E.; Wolf, E. Moran. J. Angew. Chem., 2017, 129(11), 3131-3135.
(b) Mo, X.; Yakiwchuk, J.; Dansereau, J.; McCubbin, J.A.; Hall, D.G. J. Am. Chem. Soc., 2015, 137(30), 9694-9703.
[http://dx.doi.org/10.1021/jacs.5b05076] [PMID: 26158198]
[9]
(a) Haubenreisser, S.; Niggemann, M. Adv. Synth. Catal., 2011, 353(2-3), 469-474.
[http://dx.doi.org/10.1002/adsc.201000768]
(b) Hikawa, H.; Suzuki, H.; Yokoyama, Y.; Azumaya, I. J. Org. Chem., 2013, 78(13), 6714-6720.
[http://dx.doi.org/10.1021/jo401064f] [PMID: 23745757]
(c) Kobayashi, S.; Komoto, I.; Matsuo, J-I. Adv. Synth. Catal., 2001, 343(1), 71-74.
[http://dx.doi.org/10.1002/1615-4169(20010129)343:1<71:AID-ADSC71>3.0.CO;2-J]
(d) Motokura, K.; Nakagiri, N.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Org. Chem., 2007, 72(16), 6006-6015.
[http://dx.doi.org/10.1021/jo070416w] [PMID: 17629333]
(a) Ohshima, T.; Nakahara, Y.; Ipposhi, J.; Miyamoto, Y.; Mashima, K. Chem. Commun. Camb., 2011, 47(29), 8322-8324.
[http://dx.doi.org/10.1039/c1cc12760h] [PMID: 21695315]
[10]
(a) Müller, T.E.; Beller, M. Chem. Rev., 1998, 98(2), 675-704.
[http://dx.doi.org/10.1021/cr960433d] [PMID: 11848912]
(b) Katwatsura, M.; Hartwig, J.F. J. Am. Chem. Soc., 2000, 122(39), 9546-9547.
[http://dx.doi.org/10.1021/ja002284t]
[11]
(a) Anderson, L.L.; Arnold, J.; Bergman, R.G. J. Am. Chem. Soc., 2005, 127(42), 14542-14543.
[http://dx.doi.org/10.1021/ja053700i] [PMID: 16231885]
(b) Beller, M.; Thielb, O.R.; Trauthwein, H. Synlett, 1999, 1999(2), 243-245.
[http://dx.doi.org/10.1055/s-1999-2579]
(c) Cherian, A.E.; Domski, G.J.; Rose, J.M.; Lobkovsky, E.B.; Coates, G.W. Org. Lett., 2005, 7(23), 5135-5137.
[http://dx.doi.org/10.1021/ol051916j] [PMID: 16268521]
(d) Kaspar, L.T.; Fingerhut, B.; Ackermann, L. Angew. Chem., 2005, 117(37), 6126-6128.
[http://dx.doi.org/10.1002/ange.200501423]
[12]
(a) Yao, C-H.; Song, J-S.; Chen, C-T.; Yeh, T-K.; Hsieh, T-C.; Wu, S-H.; Huang, C-Y.; Huang, Y-L.; Wang, M-H.; Liu, Y-W.; Tsai, C-H.; Kumar, C.R.; Lee, J-C. Eur. J. Med. Chem., 2012, 55, 32-38.
[http://dx.doi.org/10.1016/j.ejmech.2012.06.053] [PMID: 22818040]
(b) Reeves, J.T.; Fandrick, D.R.; Tan, Z.; Song, J.J.; Rodriguez, S.; Qu, B.; Kim, S.; Niemeier, O.; Li, Z.; Byrne, D.; Campbell, S.; Chitroda, A.; DeCroos, P.; Fachinger, T.; Fuchs, V.; Gonnella, N.C.; Grinberg, N.; Haddad, N.; Jäger, B.; Lee, H.; Lorenz, J.C.; Ma, S.; Narayanan, B.A.; Nummy, L.J.; Premasiri, A.; Roschangar, F.; Sarvestani, M.; Shen, S.; Spinelli, E.; Sun, X.; Varsolona, R.J.; Yee, N.; Brenner, M.; Senanayake, C.H. J. Org. Chem., 2013, 78(8), 3616-3635.
[http://dx.doi.org/10.1021/jo400079z] [PMID: 23544738]
(c) Sallam, A.A.; Ayoub, N.M.; Foudah, A.I.; Gissendanner, C.R.; Meyer, S.A.; El Sayed, K.A. Eur. J. Med. Chem., 2013, 70, 594-606.
[http://dx.doi.org/10.1016/j.ejmech.2013.09.045] [PMID: 24211635]
(d) Meng, S-S.; Tang, X.; Luo, X.; Wu, R.; Zhao, J-L.; Chan, A.S.C. ACS Catal., 2019, 9(9), 8397-8403.
[http://dx.doi.org/10.1021/acscatal.9b03038]
[13]
(a) Kochanowska-Karamyan, A.J.; Hamann, M.T. Chem. Rev., 2010, 110(8), 4489-4497.
[http://dx.doi.org/10.1021/cr900211p] [PMID: 20380420]
(b) Zheng, H-F.; Liu, X-H.; Xu, C-R.; Xia, Y. Angew. Chem., 2015, 127(37), 11108-11112.
[http://dx.doi.org/10.1002/ange.201505717]
[14]
(a) Fandrick, D.R.; Hart, C.A.; Okafor, I.S.; Mercadante, M.A.; Sanyal, S.; Masters, J.T.; Sarvestani, M.; Fandrick, K.R.; Stockdill, J.L.; Grinberg, N.; Gonnella, N.; Lee, H.; Senanayake, C.H. Org. Lett., 2016, 18(23), 6192-6195.
[http://dx.doi.org/10.1021/acs.orglett.6b03253] [PMID: 27934338]
(b) Wu, H.; He, Y.P.; Shi, F. Synthesis, 2015, 47(14), 1990-2016.
[http://dx.doi.org/10.1055/s-0034-1378837]
(c) Bandini, M. Angew. Chem. Int. Ed., 2009, 48(51), 9608-9644.
(d) Angew. Chem., 2009, 121(51), 9786-9824.
(e) Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett, 2005, 2005(8), 1199-1222.
[http://dx.doi.org/10.1055/s-2005-865210]
(f) Barluenga, J.; Rodríguez, F.; Fañanás, F. J. Chem. Asian J., 2009, 4(7), 1036-1048.
[http://dx.doi.org/10.1002/asia.200900018] [PMID: 19360759]
(g) Khan, I.; Sharma, A.; Kamboj, P.; Maity, B.; Tyagi, V. ChemistrySelect, 2020, 5(2), 591-600.
[http://dx.doi.org/10.1002/slct.201903863]
(h) Dong, W.; Qi, L.; Song, J-Y.; Chen, J-M.; Guo, J-X.; Shen, S.; Li, L-J.; Li, W. Org. Lett., 2019.
[http://dx.doi.org/10.1021/acs.orglett.0c00158] [PMID: 32073279]
(i) Liu, K.; Song, W.; Deng, Y.; Yang, H.; Song, C.; Abdelilah, T.; Wang, S.; Cong, H.; Tang, S.; Lei, A.; Wang, L-J. Nat. Commun., 2020, 11(1), 3.
[http://dx.doi.org/10.1038/s41467-019-13829-4] [PMID: 31911586]
[15]
(a) Mei, G-J.; Shi, F. J. Org. Chem., 2017, 82(15), 7695-7707.
[http://dx.doi.org/10.1021/acs.joc.7b01458] [PMID: 28708396]
(b) Wang, L.; Chen, Y.; Xiao, J. Asian J. Org. Chem., 2014, 3(10), 1036-1052.
[http://dx.doi.org/10.1002/ajoc.201402093]
[16]
(a) Ling, Y.; An, D.; Zhou, Y.; Rao, W. Org. Lett., 2019, 21(9), 3396-3401.
[http://dx.doi.org/10.1021/acs.orglett.9b01135] [PMID: 31008615]
(b) Xiao, J.; Wen, H.; Wang, L.; Xu, L.; Hao, Z.; Shao, C-L.; Wang, C-Y. Green Chem., 2016, 18(4), 1032-1037.
[http://dx.doi.org/10.1039/C5GC01838B]
[17]
Nallagonda, R.; Rehan, M.; Ghorai, P. J. Org. Chem., 2014, 79(7), 2934-2943.
[http://dx.doi.org/10.1021/jo4028598] [PMID: 24601671]
[18]
Suárez, A.; Martínez, F.; Sanz, R. Org. Biomol. Chem., 2016, 14(47), 11212-11219.
[http://dx.doi.org/10.1039/C6OB02125E] [PMID: 27841890]
[19]
www.ccdc.cam.ac.uk/data_request/cif
[20]
Kato, K.; Katayama, M.; Gautam, R.K.; Fujii, S.; Kimoto, H. J. Ferment. Bioeng., 1996, 76(3), 178-183.
[http://dx.doi.org/10.1016/0922-338X(93)90004-R]

Rights & Permissions Print Cite
Article Metrics
17
1
© 2024 Bentham Science Publishers | Privacy Policy