Issue 39, 2008
From the journal:

Dalton Transactions

Metal-catalyzed nucleophilic carbon–heteroatom (C–X) bond formation: the role of M–X intermediates

David S. Glueck*a  

* Corresponding authors

a 6128 Burke Laboratory, Department of Chemistry, Dartmouth College, Hanover, New Hampshire, USA
E-mail: glueck@dartmouth.edu
Fax: +1-603-646-3946
Tel: +1-603-646-1568

Abstract

Many important reactions that lead to carbon–heteroatom bond formation involve attack of anionic heteroatom nucleophiles, such as hydroxides, alkoxides, amides, thiolates and phosphides, at carbon. Related catalytic transformations are mediated by late transition metal complexes of these groups, which remain nucleophilic on metal coordination as a result of repulsive filled–filled interactions between the heteroatom lone pairs and metal d-orbitals and/or of polarization of the bonds Mδ+–Xδ−. This Perspective presents examples of catalytic nucleophilic C–X bond formation in both biological and synthetic systems and describes how changes in the metal, ancillary ligands and X groups may be used to tune nucleophilic reactivity.

Graphical abstract: Metal-catalyzed nucleophilic carbon–heteroatom (C–X) bond formation: the role of M–X intermediates

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Article information

DOI
https://doi.org/10.1039/B806138F
Article type
Perspective
Submitted
11 Apr 2008
Accepted
20 May 2008
First published
24 Jul 2008

Dalton Trans., 2008, 5276-5286

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Metal-catalyzed nucleophilic carbon–heteroatom (C–X) bond formation: the role of M–X intermediates

D. S. Glueck, Dalton Trans., 2008, 5276 DOI: 10.1039/B806138F

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