4.8 Article

A Palladium-Catalyzed Three-Component-Coupling Strategy for the Differential Vicinal Diarylation of Terminal 1,3-Dienes

Journal

ORGANIC LETTERS
Volume 16, Issue 17, Pages 4666-4669

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol502279u

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Funding

  1. National Institute of General Medical Science of the National Institutes of Health [R01GM063540, F32GM099254]
  2. National Council for Scientific and Technological Development of Brazil (CNPq)

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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 degrees C, good enantioselectivity has also been achieved.

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