Strain-promoted S-arylation and alkenylation of sulfinamides using arynes and cyclic alkynes

Zou，Xi1; Shen，Boming2; Li，Gao lin1; Liang，Qian1; Ouyang，Yanhua1; Yang，Binghe1; Yu，Peiyuan2; Gao，Bing1

2024

10.1007/s11426-023-1842-8

Science China Chemistry   影响因子和分区

1674-7291

1869-1870

The conversion of commercially available chiral sulfinamides into pharmaceutically useful chiral sulfoximines via direct S -functionalization is synthetically attractive but challenging due to the competitive reaction of N-functionalization. Herein, we disclose a novel strain-release strategy to access stereospecific and chemoselective S -arylation and alkenylation of sulfinamides using arynes and strained cyclic alkynes. This method tolerates an unprecedented chemical diversity of functional groups attached to the nitrogen center (N–R). The origin of the high S-selectivity is elucidated by density functional theory calculations, suggesting a stepwise mechanism for the aryne substrates and a concerted mechanism for the cyclic alkynes.

alkenylation arylation arynes sulfinamides sulfoximines

SCI ; EI

英语

其他

2-s2.0-85182986307

Scopus

1.State Key Laboratory of Chemo/Bio-Sensing and Chemometrics,College of Chemistry and Chemical Engineering,Institute of Chemical Biology and Nanomedicine,Hunan University,Changsha,410082,China
2.Department of Chemistry and Shenzhen Grubbs Institute,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China

Zou，Xi,Shen，Boming,Li，Gao lin,et al. Strain-promoted S-arylation and alkenylation of sulfinamides using arynes and cyclic alkynes[J]. Science China Chemistry,2024,67(3):928-935.

Zou，Xi.,Shen，Boming.,Li，Gao lin.,Liang，Qian.,Ouyang，Yanhua.,...&Gao，Bing.(2024).Strain-promoted S-arylation and alkenylation of sulfinamides using arynes and cyclic alkynes.Science China Chemistry,67(3),928-935.

Zou，Xi,et al."Strain-promoted S-arylation and alkenylation of sulfinamides using arynes and cyclic alkynes".Science China Chemistry 67.3(2024):928-935.