Regioselective Access to alpha-Vinylsilanes and alpha-Vinylgermanes by Cobalt-Catalyzed Migratory Hydrofunctionalization of 2-Alkynes

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While migratory functionalization of alkynes has been recognized as a unique way to access allylic functionalities via pi-allyl metal intermediates, hydrofunctionalization of pi-alkynes to afford alpha-functional olefins has been unexplored. We describe herein the use of a cobalt hydride based system for regioselective migratory hydrofunctionalization of 2-alkynes to furnish alpha-vinylsilanes and alpha-vinylgermanes by a mechanistic understanding of the cobalt hydride species on alkyne pi-bond migration. The key mechanism of alkyne pi-bond migration by [bis(dicyclohexylphosphino)ethane]cobalt hydride is strongly supported by both experimental and computational studies, and the role of each reaction component, such as alkynes and silanes, is elucidated to rationalize the unique alpha-vinyl selectivity.
Publisher
AMER CHEMICAL SOC
Issue Date
2021-10
Language
English
Article Type
Article
Citation

ACS CATALYSIS, v.11, no.20, pp.12777 - 12784

ISSN
2155-5435
DOI
10.1021/acscatal.1c03769
URI
http://hdl.handle.net/10203/289381
Appears in Collection
CH-Journal Papers(저널논문)
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