Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes

Yongquan Ning; Qinghe Ji; Peiqiu Liao; Edward A Anderson; Xihe Bi

doi:10.1002/anie.201705122

Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes

Angew Chem Int Ed Engl. 2017 Oct 23;56(44):13805-13808. doi: 10.1002/anie.201705122. Epub 2017 Jul 7.

Authors

Yongquan Ning¹, Qinghe Ji¹, Peiqiu Liao¹, Edward A Anderson², Xihe Bi^{1

3}

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, China.
² Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
³ State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.

Abstract

A silver-catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN₃ is reported. This three-component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. The method enables the stereoselective synthesis of a wide range of β-sulfonyl enamines without electron-withdrawing groups on the nitrogen atom. These enamines are found to be suitable for a variety of further transformations.

Keywords: alkynes; aminosulfonylation; radical reactions; silver catalysis; stereoselectivity.

Publication types

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