Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes

Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes
Qinghe Ji, Yongquan Ning, Peiqiu Liao, Xihe Bi, Edward A. Anderson
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. Controllable assembly: The first intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN3 is reported. This three-component coupling, which shows excellent functional group tolerance, proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. This enables the stereoselective synthesis of a wide range of β-sulfonyl N-unprotected enamines.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201705122

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