Issue 24, 2015

Nickel complexes for catalytic C–H bond functionalization

Abstract

The direct catalytic functionalization of traditionally unreactive C–H bonds is an atom-economic transformation that has become increasingly important and commonplace in synthetic applications. In general, 2nd and 3rd row transition metal complexes are used as catalysts in these reactions, whereas the less costly and more abundant 1st row metal complexes have limited utility. This Perspective article summarizes progress from our laboratory towards understanding the fundamental issues that complicate the use of Ni complexes for catalytic C–H bond functionalization, as well as approaches to overcoming these limitations. In practice it is found that Ni complexes can functionalize C–H bonds by processes that, to date, have not been observed with the heavier metals. An example is provided by the catalytic stannylation of C–H bonds with tributylvinyltin, Bu3SnCH[double bond, length as m-dash]CH2, which produces ethylene as a by-product.

Graphical abstract: Nickel complexes for catalytic C–H bond functionalization

Article information

Article type
Perspective
Submitted
05 Jan 2015
Accepted
02 Feb 2015
First published
24 Feb 2015

Dalton Trans., 2015,44, 10905-10913

Author version available

Nickel complexes for catalytic C–H bond functionalization

S. A. Johnson, Dalton Trans., 2015, 44, 10905 DOI: 10.1039/C5DT00032G

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