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Synfacts 2015; 11(1): 0077
DOI: 10.1055/s-0034-1379661
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Cross-Coupling of 1,1-Diboronates

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Li H, Zhang Z, Shangguan X, Huang S, Chen J, Zhang Y, Wang J * Beijing Institute of Microchemistry and Peking University, Beijing, P. R. of China
Palladium(0)-Catalyzed Cross-Coupling of 1,1-Diboronates with Vinyl Bromides and 1,1-Dibromoalkenes.

Angew. Chem. Int. Ed. 2014;
53: 11921-11925
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

palladium - cross-coupling

Significance

The authors demonstrate a palladium(0)-catalyzed reaction of 1,1-diboronates with substituted vinyl bromides or dibromoalkenes to give 1,4-dienes or allenes in good yields while showing good functional group tolerance.


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Comment

When using 1,1-dibromoalkenes bearing a terminal alkynyl group as the substrate, the palladium(0)-catalyzed coupling described above can be followed by a CuI-catalyzed allenation with N-tosylhydrazones to give unsymmetrical diallenes.


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