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. 2014 Sep 5;16(17):4666-9.
doi: 10.1021/ol502279u. Epub 2014 Aug 27.

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

Benjamin J Stokes  1 , Longyan Liao, Aline Mendes de Andrade, Qiaofeng Wang, Matthew S Sigman
Affiliations

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

Benjamin J Stokes et al. Org Lett. .

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.

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Figures

Scheme 1
Scheme 1. Three-Component-Couplings of Terminal 1,3-Dienes
Figure 1
Figure 1
Exploration of the scope of coupling partners in the three-component diarylation of terminal 1,3-butadienes. The isolated yield of each product is reported.
Figure 2
Figure 2
Reoptimized enantioselective diphenylations of (E)-1-aryl-1,3-dienes at −20 °C. The isolated yield and enantiomeric excess (as determined by SFC) for each product are reported.
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