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

ZnCl2/PhI=O Mediated Selective ortho-Chlorination of Amides

Author(s): Haixuan Liu and Qiang Sha*

Volume 19, Issue 3, 2022

Published on: 24 June, 2021

Page: [173 - 180] Pages: 8

DOI: 10.2174/1570178618666210624115748

Price: $65

Abstract

A new ortho-chlorination system consisting of zinc(II) and hypervalent iodine(III) reagent was developed for ortho-chlorination of amides, and the desired products were obtained in moderate to good yields (38-85%). This highly facile and convenient methodology is tolerant of aromatic amide and alkyl amide with diverse substituted groups. A plausible mechanism has been illustrated, in which carbocation rearrangement and metal salt coordinate facilitated orthochlorination are involved.

Keywords: Zinc, hypervalent iodine, ortho-chlorination, amide, carbocation, selectivity.

Next »
Graphical Abstract

[1]
(a) Davies, H.M.L.; Manning, J.R. Nature, 2008, 451(7177), 417-424. For selected reviews, see:
[http://dx.doi.org/10.1038/nature06485] [PMID: 18216847]
(b) Lyons, T.W.; Sanford, M.S. Chem. Rev., 2010, 110(2), 1147-1169.
[http://dx.doi.org/10.1021/cr900184e] [PMID: 20078038]
(c) Davies, H.M.L.; Du Bois, J.; Yu, J.Q. Chem. Soc. Rev., 2011, 40(4), 1855-1856.
[http://dx.doi.org/10.1039/c1cs90010b] [PMID: 21390392]
(d) Gutekunst, W.R.; Baran, P.S. Chem. Soc. Rev., 2011, 40(4), 1976-1991.
[http://dx.doi.org/10.1039/c0cs00182a] [PMID: 21298176]
(e) Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev., 2015, 44(5), 1155-1171.
[http://dx.doi.org/10.1039/C4CS00288A] [PMID: 25417560]
(f) Guo, X.X.; Gu, D.W.; Wu, Z.; Zhang, W. Chem. Rev., 2015, 115(3), 1622-1651.
[http://dx.doi.org/10.1021/cr500410y ] [PMID: 25531056]
[2]
(a) Jiang, L.; Buchwald, S.L. Metal-Catalyzed Cross Coupling Reactions 2nd ed; Diederich, F.; Stang, P.J., Eds.; WileyVCH: Weinheim, Germany, 2004, pp. 699-760
[http://dx.doi.org/ 10.1002/9783527619535.ch13]
(b) Miyaura, N.; Suzuki, A. Chem. Rev., 1995, 95, 2457-2483.
[http://dx.doi.org/ 10.1021/cr00039a007]
(c) Nicolaou, K.C.; Bulger, P.G.; Sarlah, D. Angew. Chem. Int. Ed., 2005, 44, 4442-4489.
[http://dx.doi.org/10.1002/anie.200500368]
[3]
(a) Ghose, A.K.; Viswanadhan, V.N.; Wendoloski, J.J. J. Comb. Chem., 1999, 1(1), 55-68.
[http://dx.doi.org/10.1021/cc9800071] [PMID: 10746014]
(b) Carey, J.S.; Laffan, D.; Thomson, C.; Williams, M.T. Org. Biomol. Chem., 2006, 4(12), 2337-2347.
[http://dx.doi.org/10.1039/b602413k] [PMID: 16763676]
[4]
(a) Gu, L.Q.; Lu, T.; Zhang, M.Y.; Tou, L.J.; Zhang, Y.G. Adv. Synth. Catal., 2013, 355, 1077-1082.
[http://dx.doi.org/10.1002/adsc.201300062]
(b) Huang, B.; Zhao, Y.; Yang, C.; Gao, Y.; Xia, W. Org. Lett., 2017, 19(14), 3799-3802.
[http://dx.doi.org/10.1021/acs.orglett.7b01427] [PMID: 28661678]
(c) Fosu, S.C.; Hambira, C.M.; Chen, A.D.; Fuchs, J.R.; Nagib, D.A. Chem, 2019, 5(2), 417-428.
[http://dx.doi.org/10.1016/j.chempr.2018.11.007] [PMID: 31032461]
(d) Düsel, S.J.S.; König, B. Eur. J. Org. Chem, 2020, 1491-1495.
(e) Nishii, Y.; Ikeda, M.; Hayashi, Y.; Kawauchi, S.; Miura, M. J. Am. Chem. Soc., 2020, 142(3), 1621-1629.
[http://dx.doi.org/10.1021/jacs.9b12672] [PMID: 31868360]
(f) Song, S.; Li, X.Y.; Wei, J.L.; Wang, W.J.; Zhang, Y.Q.; Ai, L.S.; Zhu, Y.C.; Shi, X.M.; Zhang, X.H.; Jiao, N. Nat. Catal., 2020, 3, 107-115. 2020, 3, 107-115.
[5]
Sun, X.; Sun, Y.; Zhang, C.; Rao, Y. Chem. Commun. (Camb.), 2014, 50(10), 1262-1264.
[http://dx.doi.org/10.1039/C3CC47431C] [PMID: 24336469]
[6]
(a) Zhang, Q.; Yang, F.; Wu, Y. J. Org. Chem. Front., 2014, 1, 694-697.
[http://dx.doi.org/10.1039/C4QO00076E]
(b) Qian, G.; Hong, X.; Liu, B.; Mao, H.; Xu, B. Org. Lett., 2014, 16(20), 5294-5297.
[http://dx.doi.org/10.1021/ol502447w] [PMID: 25251224]
(c) Kang, K.; Lee, S.; Kim, H. Asian J. Org. Chem., 2015, 4, 137-140.
[http://dx.doi.org/10.1002/ajoc.201402284]
[7]
Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc., 2006, 128(23), 7416-7417.
[http://dx.doi.org/10.1021/ja060232j] [PMID: 16756276]
[8]
Bedford, R.B.; Engelhart, J.U.; Haddow, M.F.; Mitchell, C.J.; Webster, R.L. Dalton Trans., 2010, 39(43), 10464-10472.
[http://dx.doi.org/10.1039/c0dt00385a] [PMID: 20931130]
[9]
(a) Bedford, R.B.; Mitchell, C.J.; Webster, R.L. Chem. Commun. (Camb.), 2010, 46(18), 3095-3097.
[http://dx.doi.org/10.1039/c003074k] [PMID: 20424748]
(b) Bedford, R.B.; Haddow, M.F.; Mitchell, C.J.; Webster, R.L. Angew. Chem. Int. Ed., 2011, 50, 5524-5527.
[http://dx.doi.org/10.1002/anie.201101606]
(c) Moghaddam, F.M.; Tavakoli, G.; Saeednia, B.; Langer, P.; Jafari, B. J. Org. Chem., 2016, 81(9), 3868-3876.
[http://dx.doi.org/10.1021/acs.joc.6b00329] [PMID: 27072283]
[10]
Urones, B.; Martínez, Á.M.; Rodríguez, N.; Arrayás, R.G.; Carretero, J.C. Chem. Commun. (Camb.), 2013, 49(94), 11044-11046.
[http://dx.doi.org/10.1039/c3cc47174h] [PMID: 24136684]
[11]
Monzón, G.; Tirotta, I.; Knochel, P. Angew. Chem. Int. Ed., 2012, 51, 10624-10627.
[http://dx.doi.org/10.1002/anie.201205465]
[12]
(a) Kathiravan, S.; Nicholls, I.A. Chemistry, 2017, 23(29), 7031-7036.
[http://dx.doi.org/10.1002/chem.201700280] [PMID: 28221698]
(b) Li, Z.L.; Sun, K.K.; Cai, C. Org. Biomol. Chem., 2018, 16(30), 5433-5440.
[http://dx.doi.org/10.1039/C8OB01448E] [PMID: 30019056]
[13]
(a) Schröder, N.; Wencel-Delord, J.; Glorius, F. J. Am. Chem. Soc., 2012, 134(20), 8298-8301.
[http://dx.doi.org/10.1021/ja302631j] [PMID: 22548632]
(b) Sun, X.Y.; Shan, G.; Sun, Y.H.; Rao, Y. Angew. Chem. Int. Ed., 2013, 52, 4440-4444.
[http://dx.doi.org/10.1002/anie.201300176]
[14]
(a) Barret, R.; Daudon, M. Tetrahedron Lett., 1991, 32, 2133-2134.
[http://dx.doi.org/10.1016/S0040-4039(00)71255-X]
(b) Singh, F.V.; Wirth, T. Synthesis, 2013, 45, 2499-2511. For a review, see:
[http://dx.doi.org/10.1055/s-0032-1316917]
[15]
(a) Dohi, T.; Kita, Y. Chem. Commun. (Camb.), 2009, (16), 2073- 2085. For selected reviews, see:
[http://dx.doi.org/10.1039/b821747e] [PMID: 19360157]
(b) Charpentier, J.; Früh, N.; Togni, A. Chem. Rev., 2015, 115(2), 650-682.
[http://dx.doi.org/10.1021/cr500223h] [PMID: 25152082]
(c) Yoshimura, A.; Zhdankin, V.V. Chem. Rev., 2016, 116(5), 3328-3435.
[http://dx.doi.org/10.1021/acs.chemrev.5b00547] [PMID: 26861673]
(d) Parra, A. Chem. Rev., 2019, 119(24), 12033-12088.
[http://dx.doi.org/10.1021/acs.chemrev.9b00338 ] [PMID: 31741377]
[16]
(a) Liu, H.X.; Wei, Y.Y. Tetrahedron Lett., 2013, 54, 4645-4648.
[http://dx.doi.org/10.1016/j.tetlet.2013.06.053]
(b) Liu, H.X.; Wei, Y.Y.; Cai, C. New J. Chem., 2016, 40, 674-678.
[http://dx.doi.org/10.1039/C5NJ02378E]
[17]
J. Chem. Soc. Trans, 1899, 75, 1046-1054. J. Org. Chem., 1987, 52, 173-175.
[18]
(a) Rivas, J.C.M.; Salvagni, E.; Prabaharan, R.; de Rosales, R.T.M.; Parsons, S. Dalton Trans., 2004, (1), 172-177.
[http://dx.doi.org/10.1039/b312221b] [PMID: 15356757]
(b) Kumar, M.P.; Liu, R.S. J. Org. Chem., 2006, 71(13), 4951-4955.
[http://dx.doi.org/10.1021/jo0606711] [PMID: 16776526]
(c) Kita, Y.; Nishii, Y.; Higuchi, T.; Mashima, K. Angew. Chem. Int. Ed., 2012, 51, 5723-5726.
[http://dx.doi.org/10.1002/anie.201201789]

Rights & Permissions Print Cite
Article Metrics
18
12
© 2024 Bentham Science Publishers | Privacy Policy