Site-selective olefinic C–H cyanation via alkenyl sulfonium salts

A chemo- and regioselective olefinic C–H cyanation strategy was developed through palladium-catalyzed C(sp2)–S bond cleavage of stable alkenyl sulfonium salts with CuCN, efficiently affording multisubstituted alkenyl nitriles (acrylonitriles). This process features broad substrate scope, good chemo-...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-08, Vol.10 (16), p.4092-4099
Main Authors: Ma, Juan, Lin, Jie, Huang, Zilong, Wu, Ping, Yong-Gui, Zhou, Yu, Zhengkun
Format: Article
Language:English
Subjects:
Acrylonitriles
Alkenes
Functional groups
Nitriles
Organic chemistry
Palladium
Regioselectivity
Substrates
Sulfonium salts
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Summary:A chemo- and regioselective olefinic C–H cyanation strategy was developed through palladium-catalyzed C(sp2)–S bond cleavage of stable alkenyl sulfonium salts with CuCN, efficiently affording multisubstituted alkenyl nitriles (acrylonitriles). This process features broad substrate scope, good chemo- and regioselectivities, and excellent functional group tolerance. The present protocol provides an alternative route to alkenyl nitriles from readily available functionalized alkenes by a site-selective interrupted Pummerer activation/palladium-catalyzed olefinic C(sp2)–S cyanation sequence.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo00833a