Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Butadiene Sulfone-catalyzed Monobromination of Arenes with NBS as the Bromination Source: A Simple, Mild, Efficient, and Chemoselective Protocol

Author(s): Amit Sharma, Santosh Rudrawar and Hemant R. Jadhav*

Volume 21, Issue 2, 2024

Published on: 06 October, 2023

Page: [201 - 208] Pages: 8

DOI: 10.2174/1570178620666230914164247

Price: $65

Abstract

In literature, dimethyl sulfoxide (DMSO) catalyzed bromination of arenes and heteroarenes is reported. In this study, simple, mild, and chemoselective N-bromosuccinimide (NBS) mediated monobromination of arenes and heteroarenes using butadiene sulfone as a catalyst is reported.

Butadiene sulfone is a good substitute for DMSO as it is volatile, easy to recover and recycle, and environment- friendly. The method has been demonstrated to give high-yield brominated products for an extensive range of activated and deactivated arenes.

Graphical Abstract

[1]
Zhang, Y.; Shibatomi, K.; Yamamoto, H. Synlett, 2005, 18, 2837-2842.
[2]
Heck, R.F.; Nolley, J.P., Jr J. Org. Chem., 1972, 37(14), 2320-2322.
[http://dx.doi.org/10.1021/jo00979a024]
[3]
Li, J.Q.; Chen, X.H.; Wang, X.X.; Cui, H.L. Tetrahedron Lett., 2021, 82, 153375.
[http://dx.doi.org/10.1016/j.tetlet.2021.153375]
[4]
Ruiz-Castillo, P.; Buchwald, S.L. Chem. Rev., 2016, 116(19), 12564-12649.
[http://dx.doi.org/10.1021/acs.chemrev.6b00512] [PMID: 27689804]
[5]
Rao, K.U.; Lakshmidevi, J.; Appa, R.M.; Prasad, S.S.; Narasimhulu, M.; Vijitha, R.; Rao, K.S.V.K.; Venkateswarlu, K. Chemistry Select., 2017, 2(24), 7394-7398.
[http://dx.doi.org/10.1002/slct.201701413]
[6]
Lakshmidevi, J.; Appa, R.M.; Naidu, B.R.; Prasad, S.S.; Sarma, L.S.; Venkateswarlu, K. Chem. Commun., 2018, 54(87), 12333-12336.
[http://dx.doi.org/10.1039/C8CC06940A]
[7]
Sun, H.; Keefer, C, E.; Scott D, O. Drug Metab. Lett., 2011, 4, 232-242.
[http://dx.doi.org/10.2174/187231211798472575] [PMID: 21916842]
[8]
Song, S.; Sun, X.; Li, X.; Yuan, Y.; Jiao, N. Org. Lett., 2015, 17(12), 2886-2889.
[http://dx.doi.org/10.1021/acs.orglett.5b00932] [PMID: 26010555]
[9]
Kajita, H.; Togni, A. Chemistry Select., 2017, 2(3), 1117-1121.
[http://dx.doi.org/10.1002/slct.201700024]
[10]
Shao, H.; Wang, X.; Wang, Y.; Yue, Y.; Wang, K.; Tang, Q.; Zhuo, K.; Liu, J. Chemistry Select., 2019, 4(31), 8942-8945.
[http://dx.doi.org/10.1002/slct.201902492]
[11]
Rogers, D.A.; Brown, R.G.; Brandeburg, Z.C.; Ko, E.Y.; Hopkins, M.D.; LeBlanc, G.; Lamar, A.A. ACS Omega., 2018, 3(10), 12868-12877.
[http://dx.doi.org/10.1021/acsomega.8b02320] [PMID: 31458011]
[12]
Ni, S.; El Remaily, M.A.E.A.A.A.; Franzén, J. Adv. Synth. Catal., 2018, 360(21), 4197-4204.
[http://dx.doi.org/10.1002/adsc.201800788]
[13]
Roche, D.; Prasad, K.; Repic, O.; Blacklock, T.J. Tetrahedron Lett., 2000, 41(13), 2083-2085.
[http://dx.doi.org/10.1016/S0040-4039(00)00119-2]
[14]
Konishi, H.; Aritomi, K.; Okano, T.; Kiji, J. Bull. Chem. Soc. Jpn., 1989, 62(2), 591-593.
[http://dx.doi.org/10.1246/bcsj.62.591]
[15]
Huang, Y.; Ureña-Benavides, E.E.; Boigny, A.J.; Campbell, Z.S.; Mohammed, F.S.; Fisk, J.S.; Holden, B.; Eckert, C.A.; Pollet, P.; Liotta, C.L. Sustainable Chemical Processes., 2015, 1, 1-10.

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