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Issue 4, 2014
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Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

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Abstract

Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C–C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

Graphical abstract: Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

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Supplementary files

Article information


Submitted
04 Nov 2013
Accepted
28 Nov 2013
First published
29 Nov 2013

Chem. Sci., 2014,5, 1361-1367
Article type
Edge Article

Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

C. Vila, M. Giannerini, V. Hornillos, M. Fañanás-Mastral and B. L. Feringa, Chem. Sci., 2014, 5, 1361
DOI: 10.1039/C3SC53047G

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