Issue 29, 2012
From the journal:

Organic & Biomolecular Chemistry

Rhodium(iii)-catalyzed oxidative mono- and di-olefination of isonicotinamides†

Xiaohong Wei,ab   Feng Wang,a   Guoyong Song,a   Zhengyin Dub  and  Xingwei Li*a  

* Corresponding authors

a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P.R. China

b College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P.R. China
E-mail: xwli@dicp.ac.cn

Abstract

[RhCp*Cl2]2 can catalyze the oxidative coupling of secondary isonicotinamides with activated olefins using Cu(OAc)2 as an oxidant. The selectivity can be controlled by the solvent. In MeCN, the mono-olefination and two-fold oxidation reaction is the major pathway, while in THF this reaction gave mostly diolefination products. In both cases, the coupled products contain an exocyclic C[double bond, length as m-dash]C bond.

Graphical abstract: Rhodium(iii)-catalyzed oxidative mono- and di-olefination of isonicotinamides

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Article information

DOI
https://doi.org/10.1039/C2OB25773D
Article type
Communication
Submitted
23 Apr 2012
Accepted
08 Jun 2012
First published
13 Jun 2012

Org. Biomol. Chem., 2012,10, 5521-5524

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Rhodium(III)-catalyzed oxidative mono- and di-olefination of isonicotinamides

X. Wei, F. Wang, G. Song, Z. Du and X. Li, Org. Biomol. Chem., 2012, 10, 5521 DOI: 10.1039/C2OB25773D

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