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Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism.
- Source :
-
European Journal of Organic Chemistry . 9/1/2017, Vol. 2017 Issue 32, p4758-4764. 7p. - Publication Year :
- 2017
-
Abstract
- The substrate scope and the mechanism have been investigated for the MnCl2-catalyzed cross-coupling reaction between aryl halides and Grignard reagents. The transformation proceeds rapidly and in good yield when the aryl halide component is an aryl chloride containing a cyano or an ester group in the para position or a cyano group in the ortho position. A range of other substituents gave no conversion of the aryl halide or led to the formation of side products. A broader scope was observed for the Grignard reagents, where a variety of alkyl- and arylmagnesium chlorides participated in the coupling. Two radical-clock experiments were carried out, and in both cases an intermediate aryl radical was successfully trapped. The cross-coupling reaction is therefore believed to proceed by an SRN¹ mechanism, with a triorganomanganate complex serving as the most likely nucleophile and single-electron donor. Other mechanistic scenarios were excluded based on the substrate scope of the aryl halide. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2017
- Issue :
- 32
- Database :
- Academic Search Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 124888965
- Full Text :
- https://doi.org/10.1002/ejoc.201700981