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Issue 13, 2013
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sp2 C–H bond activation in water and catalytic cross-coupling reactions

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Abstract

The metal-catalysed successive activation and functionalisation of sp2 C–H bonds is the at heart of synthetic innovations for the development of C–C bond cross-coupling processes. Against expectation catalytic C–H bond transformations can be performed in water as an available, renewable, safe solvent but most importantly as a partner improving the catalyst activity. The objective of the review is to present the catalytic successes for C–H bond transformations in water, discovered mainly during the last six years and involving mostly palladium and ruthenium catalysts, often with the help of a carboxylate partner for the initial key C–H bond deprotonation. Water is beneficial for the direct catalytic arylation with (hetero)aryl halides of functional arene ortho C–H bonds with pyridine, pyrazole, oxazoline, imine, urea, amide… directing groups leading to functional biaryl derivatives, polyheterocycles and polydentate ligands. Metal-catalysed activation of the sp2 C–H bond in water also allows the cross-coupling reaction of two different C–H bonds in the presence of an oxidant and regioselective alkenylations of arenes, heterocycles and functional alkenes are now controlled. Annulation reactions via insertion of alkynes into both activated C–H and heteroatom–hydrogen bonds in water constitute new routes to heterocycles.

Graphical abstract: sp2 C–H bond activation in water and catalytic cross-coupling reactions

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Article information


Submitted
23 Jan 2013
First published
25 Mar 2013

Chem. Soc. Rev., 2013,42, 5744-5767
Article type
Review Article

sp2 C–H bond activation in water and catalytic cross-coupling reactions

B. Li and P. H. Dixneuf, Chem. Soc. Rev., 2013, 42, 5744
DOI: 10.1039/C3CS60020C

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