Issue 4, 2014

Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents

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

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Nov 2013
Accepted
28 Nov 2013
First published
29 Nov 2013

Chem. Sci., 2014,5, 1361-1367

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements