(Fluoromethylsulfonyl)methylation of Quinoxalinones Using NaSO2CH2F for C-F Bond Cleavage

Peng Dai; Yufei Li; Yu Chen; Jian Jiao; Qingqing Wang; Chenxiao Li; Yucheng Gu; Yanbin Zhang; Qing Xia; Wei-Hua Zhang

doi:10.1021/acs.orglett.2c00048

(Fluoromethylsulfonyl)methylation of Quinoxalinones Using NaSO₂CH₂F for C-F Bond Cleavage

Org Lett. 2022 Feb 18;24(6):1357-1361. doi: 10.1021/acs.orglett.2c00048. Epub 2022 Feb 5.

Authors

Peng Dai¹, Yufei Li¹, Yu Chen¹, Jian Jiao¹, Qingqing Wang¹, Chenxiao Li¹, Yucheng Gu², Yanbin Zhang³, Qing Xia¹, Wei-Hua Zhang¹

Affiliations

¹ Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China.
² Syngenta Jealott's Hill International Research Centre, Bracknell RG42 6EY, U.K.
³ Department of Chemistry, National University of Singapore, 117545 Singapore.

PMID: 35128927
DOI: 10.1021/acs.orglett.2c00048

Abstract

We developed a facile, efficient, and scalable route to achieve monofluoromethylsulfinyl alkylation of quinoxalinones. NaSO₂CH₂F served as the source of methylene to construct new C-C and C-S bonds via C-F bond cleavage. NaSO₂CH₂F was also the source of SO₂CH₂F. Density functional theory calculations confirmed the proposed mechanism, in which the SO₂CH₂F radical is immediately trapped. The reaction exhibited a high level of atom economy. Moreover, some representative products displayed excellent biological activity.

Publication types

Research Support, Non-U.S. Gov't