I2/PhI(OAc)2 Copromoted Amination Reaction: Synthesis of α-Dicarbonylsulfoximine Derivatives by Incorporating an Intact Dimethyl Sulfoxide

Peng Zhao; Xia Wu; Xiao Geng; Can Wang; You Zhou; Yan-Dong Wu; An-Xin Wu

doi:10.1021/acs.joc.9b01160

I₂/PhI(OAc)₂ Copromoted Amination Reaction: Synthesis of α-Dicarbonylsulfoximine Derivatives by Incorporating an Intact Dimethyl Sulfoxide

J Org Chem. 2019 Jun 21;84(12):8322-8329. doi: 10.1021/acs.joc.9b01160. Epub 2019 Jun 11.

Authors

Peng Zhao¹, Xia Wu¹, Xiao Geng¹, Can Wang¹, You Zhou¹, Yan-Dong Wu¹, An-Xin Wu¹

Affiliation

¹ Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry , Central China Normal University , Wuhan 430079 , P.R. China.

PMID: 31140280
DOI: 10.1021/acs.joc.9b01160

Abstract

An I₂/PhI(OAc)₂ copromoted strategy using dimethyl sulfoxide as an "S/C2/O" source for preparing α-dicarbonylsulfoximine derivatives is reported. This process involves oxidative coupling to construct a C-N bond and electrophilic amination of dimethyl sulfoxide to afford an N═S bond, with dimethyl sulfoxide present in the final product as an intact molecule. Furthermore, tetramethylene sulfoxide as a solvent is also compatible with this amination reaction.

Publication types

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