作者:Jason R. Combs、David S. Carter、Fengyi Gu、Xiaokang Jin、Connor M. Martin、Elizabeth S. Resendiz、David L. Van Vranken
DOI:10.1021/acs.orglett.3c03130
日期:2023.11.17
Rhodium(II) catalyzes carbene transfer from trimethylsilyldiazomethane to arylmethyl thioethers, generating sulfonium ylides that undergo [2,3]-sigmatropic rearrangement, punching quaternary centers into aromatic rings. The reaction works well with naphthalene, indole, and benzofuran ring systems, but the reaction is unsuccessful with the monocyclic benzene homologue. For aryl thioethers, Rh2(OAc)4
铑 (II) 催化卡宾从三甲基甲硅烷基重氮甲烷转移到芳甲基硫醚,生成锍叶立德,进行 [2,3]-σ 重排,将四级中心打入芳环。该反应适用于萘、吲哚和苯并呋喃环系,但适用于单环苯同系物则不成功。对于芳基硫醚,Rh 2 (OAc) 4给出了良好的结果。对于烷基硫醚,使用Rh 2 (cap) 4可以提高收率。令人惊讶的是,硫酯和硫代氨基甲酸酯也是该反应的有效底物。