Iodine‐Mediated Coupling of Cyclic Amines with Sulfonyl Hydrazides: an Efficient Synthesis of Vinyl Sulfone Derivatives

An efficient iodine‐mediated coupling of cyclic amines with sulfonyl hydrazides is reported. This transformation opens a new route to the synthesis of vinyl sulfones derivatives, which is a common structural motif in natural products and pharmaceuticals. Tentative mechanistic studies suggest that th...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-01, Vol.2021 (4), p.701-708
Main Authors: Rong, Xiaona, Guo, Jingwen, Hu, Zheqi, Huang, Lehao, Gu, Yugui, Cai, Yuepiao, Liang, Guang, Xia, Qinqin
Format: Article
Language:English
Subjects:
Cyclic amines
Peroxide
Radicals
Sulfones
Sulfonyl hydrazides
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Summary:An efficient iodine‐mediated coupling of cyclic amines with sulfonyl hydrazides is reported. This transformation opens a new route to the synthesis of vinyl sulfones derivatives, which is a common structural motif in natural products and pharmaceuticals. Tentative mechanistic studies suggest that this reaction is likely to involve a radical process. A highly efficient and generally applicable methodology for the construction of vinyl sulfone derivatives from cyclic amines and sulfonyl hydrazides in one step was developed. This protocol could be applied for the C−S bond formation of N‐Aryl piperidines, N‐alkyl piperidines, and heteroaryl piperidines with sulfonyl hydrazides.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001510