Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles

A method for the palladium-catalyzed disilylation and digermanylation of aryl halides bearing a tethered alkene has been developed. The mechanism is thought to proceed via Heck-type cyclization, followed by C–H activation, resulting in a reactive fused-palladacycle. A wide variety of disilylated and...

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Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (9), p.3679-3683
Main Authors: Wollenburg, Marco, Bajohr, Jonathan, Marchese, Austin D, Whyte, Andrew, Glorius, Frank, Lautens, Mark
Format: Article
Language:English
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Summary:A method for the palladium-catalyzed disilylation and digermanylation of aryl halides bearing a tethered alkene has been developed. The mechanism is thought to proceed via Heck-type cyclization, followed by C–H activation, resulting in a reactive fused-palladacycle. A wide variety of disilylated and digermanylated heterocycles are obtained from readily available aryl halides in high yields with various functional groups. Moreover, the developed protocol proved to be highly diastereoselective.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01169