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Synfacts 2020; 16(07): 0823
DOI: 10.1055/s-0040-1707030
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Miyaura Borylation Reaction

Contributor(s):
Mark Lautens
,
Randy Sanichar
Ishiyama T, Murata M, Miyaura N. * Hokkaido University, Sapporo, Japan
Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters.

J. Org. Chem. 1995;
60: 7508-7510
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Further Information

Publication History

Publication Date:
17 June 2020 (online)

 
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Key words

Miyaura borylation - cross-coupling - palladium catalysis - arylboronic esters

Significance

Miyaura and co-workers reported a direct catalytic approach for the preparation of arylboronic esters from aryl halides that proceeded in excellent yields and selectivity. This palladium-catalyzed reaction proved to have a broader functional group tolerance (e.g. to ketones, esters, nitriles) than prior syntheses of these useful synthetic linchpins via reactions with organometallic reagents.


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Comment

The authors noted that the use of the KOAc as a base was critical to the formation of the desired aryl boronic esters in high yields and selectivities. They proposed that the base accelerates the transmetalation process, preventing the biaryl byproducts from being formed (see Review below).


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Review

E. C. Neeve, S. J. Geier, I. A. I. Mkhalid, S. A. Westcott, T. B. Marder Chem. Rev. 2016, 116, 9091–9161.


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