Nickel-Catalyzed Stereoselective Dicarbofunctionalization of Alkynes

A nickel‐catalyzed three‐component reaction involving terminal alkynes, boronic acids, and alkyl halides is presented herein. Trisubstituted alkenes can be obtained in a highly regio‐ and stereocontrolled manner by the simultaneous addition of both aryl and alkyl groups across the triple bond in a r...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-06, Vol.55 (24), p.6938-6941
Main Authors: Li, Zhaodong, García-Domínguez, Andrés, Nevado, Cristina
Format: Article
Language:English
Subjects:
alkyl halides
alkynes
boron
nickel
radicals
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Summary:A nickel‐catalyzed three‐component reaction involving terminal alkynes, boronic acids, and alkyl halides is presented herein. Trisubstituted alkenes can be obtained in a highly regio‐ and stereocontrolled manner by the simultaneous addition of both aryl and alkyl groups across the triple bond in a radical‐mediated process. The reaction, devoid of air‐ and moisture‐sensitive organometallic reagents and catalysts, is operationally simple and offers a broad scope and functional‐group tolerance. Triple whammy: A nickel‐catalyzed three‐component reaction involving terminal alkynes, boronic acids, and alkyl halides produces trisubstituted alkenes in a highly regio‐ and stereocontrolled fashion. The reaction, devoid of air‐ and moisture‐sensitive organometallic reagents and catalysts, is operationally simple and offers a broad scope and functional‐group tolerance.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201601296