Palladium-Catalyzed Regio- and Stereoselective Coupling–Addition of Propiolates with Arylsulfonyl Hydrazides: A Pattern for Difunctionalization of Alkynes

A new pattern for difunctionalization of alkynes via a palladium-catalyzed regio- and stereoselective coupling–addition of propiolates with arylsulfonyl hydrazides is disclosed. The approach enables the synthesis of various highly functionalized (E)-vinylsulfones in satisfactory yields. Arylsulfonyl...

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Bibliographic Details
Published in:Organic letters 2018-07, Vol.20 (13), p.4023-4027
Main Authors: Liu, Lixin, Sun, Kang, Su, Lebin, Dong, Jianyu, Cheng, Lei, Zhu, Xiaodong, Au, Chak-Tong, Zhou, Yongbo, Yin, Shuang-Feng
Format: Article
Language:English
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Summary:A new pattern for difunctionalization of alkynes via a palladium-catalyzed regio- and stereoselective coupling–addition of propiolates with arylsulfonyl hydrazides is disclosed. The approach enables the synthesis of various highly functionalized (E)-vinylsulfones in satisfactory yields. Arylsulfonyl hydrazides act as both aryl and sulfonyl sources via selective cleavage of Ar­(C)–S and S–N bonds, which are simultaneously incorporated onto the terminal carbon atom of an alkyne molecule.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b01585