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

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Seidel,  Günter
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Seidel, G., & Fürstner, A. (2012). Suzuki reactions of extended scope: the ‘9-MeO-9-BBN variant’ as a complementary format for cross-coupling. Chemical Communications, 48(15), 2055-2070. doi:10.1039/c2cc17070a.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-EFC1-F
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, alkynyl etc.) 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.