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A palladium-catalyzed three-component-coupling strategy for the differential vicinal diarylation of terminal 1,3-dienes.

ABSTRACT: A palladium-catalyzed intermolecular vicinal diarylation of terminal 1,3-dienes using aryldiazonium tetrafluoroborates and arylboronic acids is reported. Using this technology, two different arenes are regioselectively introduced in a vicinal fashion across the terminal alkene of a variety of terminal 1,3-dienes at ambient temperature. Through the action of a chiral bicyclo[2.2.2]octadienyl ligand at -20 °C, good enantioselectivity has also been achieved.

SUBMITTER: Stokes BJ 

PROVIDER: S-EPMC4156257 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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A palladium-catalyzed three-component-coupling strategy for the differential vicinal diarylation of terminal 1,3-dienes.

Stokes Benjamin J BJ   Liao Longyan L   de Andrade Aline Mendes AM   Wang Qiaofeng Q   Sigman Matthew S MS  

Organic letters 20140827 17

A palladium-catalyzed intermolecular vicinal diarylation of terminal 1,3-dienes using aryldiazonium tetrafluoroborates and arylboronic acids is reported. Using this technology, two different arenes are regioselectively introduced in a vicinal fashion across the terminal alkene of a variety of terminal 1,3-dienes at ambient temperature. Through the action of a chiral bicyclo[2.2.2]octadienyl ligand at -20 °C, good enantioselectivity has also been achieved. ...[more]

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