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Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes
Author(s) -
Ning Yongquan,
Ji Qinghe,
Liao Peiqiu,
Anderson Edward A.,
Bi Xihe
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705122
Subject(s) - chemistry , stereoselectivity , alkyne , sulfonyl , catalysis , nitrogen atom , sodium azide , intermolecular force , azide , polar effect , polymer chemistry , organic chemistry , medicinal chemistry , combinatorial chemistry , molecule , group (periodic table) , alkyl
A silver‐catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN 3 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.
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