Electrophilic amidomethylation of arenes with DMSO/MeCN reagents. Issue 9 (24th March 2022)

• Record Type: Journal Article
• Authors: Zhang, Hongliang; Wang, Weijin; Wang, Bingding; Tan, Hui; Jiao, Ning; Song, Song
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 9(2022)
• Page Start: 2430
• Page End: 2437
• Publication Date: 2022-03-24
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d2qo00181k
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An efficient electrophilic amidomethylation of aromatics was described with DMSO as the CH2 source and nitrile as the nitrogen source. Abstract : An efficient electrophilic amidomethylation of aromatics was described to construct N -benzylic amides, which are core structures in drugs and natural products. The simple combination of dimethyl sulfoxide (DMSO, as the CH2 unit) and acetonitrile (MeCN, as the nitrogen unit) as a highly active amidomethylation reagent enables the efficient C–C, C–N and CO bond construction. Notably, this method provides a practical protocol for the efficient preparation of deuterated benzylamine derivatives with easily available d 6 -DMSO or d 3 -MeCN, and is also applied in the concise synthesis of Nonivamide and Pimavanserin.