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Issue 23, 2010
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On the role of additives in alkyl–alkyl Negishi cross-couplings

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Abstract

An additives study for the alkyl–alkyl Negishi reaction using an NHC–Pd catalyst revealed that bromide salts promote coupling while the cation is mechanistically benign. A double titration revealed that the cross-coupling begins at a 1 ∶ 1 ratio of LiBrnBuZnBr, suggesting that a higher-order zincate, presumably LimZn(nBu)Br3(2−m)−, is the active transmetalating agent.

Graphical abstract: On the role of additives in alkyl–alkyl Negishi cross-couplings

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Article information


Submitted
09 Feb 2010
Accepted
02 Mar 2010
First published
19 Mar 2010

Chem. Commun., 2010,46, 4109-4111
Article type
Communication

On the role of additives in alkyl–alkyl Negishi cross-couplings

G. T. Achonduh, N. Hadei, C. Valente, S. Avola, C. J. O'Brien and M. G. Organ, Chem. Commun., 2010, 46, 4109
DOI: 10.1039/C002759F

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