Issue 15, 2012

Suzuki reactions of extended scope: the ‘9-MeO-9-BBN variant’ as a complementary format for cross-coupling

Abstract

While the Suzuki coupling has gained paramount importance, the basic set-up of the reaction has remained essentially unchanged for decades. It consists of the palladium-catalyzed coupling of organoboron reagents with aryl- or alkenyl halides, -sulfonates or related electrophiles in the presence of a base. One of the few alternative formats for this transformation is the ‘9-MeO-9-BBN variant’, which is distinguished by not requiring an added base as a promoter. Rather, polar organometallic reagents R–M (R = Me, alkyl, aryl, heteroaryl, alkenyl, alkynyletc.) are first intercepted with 9-MeO-9-BBN to give the corresponding borinate complexes, which then pass the R-group onto an organopalladium complex generated in situ as the electrophilic partner. This procedure allowed the structural reach of the Suzuki coupling to be extended, and served in a host of advanced applications, most notably for elaborate sp–sp2 and sp3–sp2 coupling processes.

Graphical abstract: Suzuki reactions of extended scope: the ‘9-MeO-9-BBN variant’ as a complementary format for cross-coupling

Article information

Article type
Feature Article
Submitted
14 Nov 2011
Accepted
05 Dec 2011
First published
12 Jan 2012

Chem. Commun., 2012,48, 2055-2070

Suzuki reactions of extended scope: the ‘9-MeO-9-BBN variant’ as a complementary format for cross-coupling

G. Seidel and A. Fürstner, Chem. Commun., 2012, 48, 2055 DOI: 10.1039/C2CC17070A

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