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The Rh(<scp>ii</scp>)-catalyzed formal N–S bond insertion reaction of aryldiazoacetates into N-phenyl-sulfenyl phthalimide

Authors :
Tao Xin
Qing-Long Xu
Chao Jin
Hongbin Sun
Xiaoan Wen
Yizhou Wu
Zhuang Song
Source :
Chemical Communications. 52:6079-6082
Publication Year :
2016
Publisher :
Royal Society of Chemistry (RSC), 2016.

Abstract

The Rh(ii)-catalyzed sulfur ylide [1,2]-rearrangement of carbenoids generated from aryldiazoacetates has been realized via N-S bond insertion, generating tertiary sulfides in moderate to excellent yields. This demonstrates the first use of the sulfur ylide [1,2]-rearrangement undergoing N-S bond insertion. This protocol could proceed smoothly with high regioselectivity, low catalyst loading (0.1 mol% Rh2(OAc)4), gram-scale reaction and broad substrate scope. And the product could be converted into glycine derivatives through simple procedures.

Details

ISSN :
1364548X and 13597345
Volume :
52
Database :
OpenAIRE
Journal :
Chemical Communications
Accession number :
edsair.doi.dedup.....9ec49f414d6fb07976f8385eb5a06a74