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Synfacts 2016; 12(3): 0261
DOI: 10.1055/s-0035-1561744
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Axially Chiral Vinyl Arenes by Palladium(0) Catalysis

Contributor(s):
Mark Lautens
,
Kosuke Yamamoto
Feng J, Li B, He Y, Gu Z * University of Science and Technology of China, Hefei, P. R. of China
Enantioselective Synthesis of Atropisomeric Vinyl Arene Compounds by Palladium Catalysis: A Carbene Strategy.

Angew. Chem. Int. Ed. 2016;
55: 2186-2190
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Publication History

Publication Date:
16 February 2016 (online)

 
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Key words

palladium catalysis - vinyl arenes - carbenes - phosphine–olefin ligands

Significance

The authors report the highly enantioselective synthesis of various vinyl arenes via a palladium-catalyzed cross-coupling reaction. The vinyl-arene compounds were easily transformed into binaphthyl skeletons or phosphine compounds. The authors also demonstrate an application of the product as a chiral phosphine–olefin ligand in an allylic substitution reaction.


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Comment

The reported coupling reaction involves oxidative addition of palladium(0) to bromoarenes, reaction with the diazo compound to generate a palladium–carbene species, migratory insertion and β-hydride elimination. A broad substrate scope was demonstrated and a range of chiral vinyl arenes were obtained. These products might be a new class of chiral phosphine–olefin ligands.


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