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Synfacts 2015; 11(7): 0749
DOI: 10.1055/s-0034-1380914
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Hydroboration of Alkynes

Contributor(s):
Paul Knochel
,
Diana Haas
Obligacion JV, Neely JM, Yazdani AN, Pappas I, Chirik PJ * Princeton University, USA
Cobalt Catalyzed Z-Selective Hydroboration of Terminal Alkynes and Elucidation of the Origin of Selectivity.

J. Am. Chem. Soc. 2015;
137: 5855-5858
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Further Information

Publication History

Publication Date:
17 June 2015 (online)

 
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Key words

cobalt - hydroboration - alkynes

Significance

Chirik and co-workers report a bis(imino)pyridine cobalt-catalyzed hydroboration of terminal alkynes using HBpin to afford various vinylboronate esters with high Z-selectivity.


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Comment

Selective insertion of an alkynylboronate ester into a Co–H bond via syn-hydrometalation generates a pro-(Z) cobalt alkenyl intermediate to yield the corresponding (Z)-vinylboronate ester.


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