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Synfacts 2017; 13(11): 1155
DOI: 10.1055/s-0036-1591388
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Hydroarylation Reaction

Contributor(s):
Mark Lautens
,
Ivan Franzoni
Kortman GD. Hull KL. * University of Illinois at Urbana–Champaign, USA
Copper-Catalyzed Hydroarylation of Internal Alkynes: Highly Regio- and Diastereoselective Synthesis of 1,1-Diaryl, Trisubstituted Olefins.

ACS Catal. 2017;
7: 6220-6224
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Publication History

Publication Date:
19 October 2017 (online)

 
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Key words

copper catalysis - trisubstituted olefins - hydroarylation

Significance

The stereoselective synthesis of trisubstituted olefins has attracted considerable attention due to the prevalence of such structural motifs in pharmaceuticals and as valuable synthetic building blocks. In this paper, the authors present a stereoselective copper-catalyzed hydroarylation of internal alkynes for the synthesis of 1,1-diaryl trisubstituted olefins.


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Comment

The combination of a copper(II) catalyst, polymethylhydrosiloxane as hydride source, and additives allowed the reaction between internal alkynes and several aryl iodides. The corresponding products were generally obtained in good to excellent yields and with high regioselectivities. Several 2.0 mmol scale reactions were demonstrated.


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