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Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism

Artikel i vetenskaplig tidskrift
Författare G. Antonacci
A. Ahlburg
P. Fristrup
Per-Ola Norrby
R. Madsen
Publicerad i European Journal of Organic Chemistry
Nummer/häfte 32
Sidor 4758-4764
ISSN 1434-193X
Publiceringsår 2017
Publicerad vid Institutionen för kemi och molekylärbiologi
Sidor 4758-4764
Språk English
Länkar doi.org/10.1002/ejoc.201700981
Ämnesord Cross-coupling, Grignard reagents, Manganese, Radical reactions, Reaction mechanisms, Earth-, nucleophilic-substitution reactions, electron-transfer, organomagnesium, reagents, anion-radicals, iodides, chlorobenzonitriles, reduction, complexes, ethers, Chemistry
Ämneskategorier Organisk kemi

Sammanfattning

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 S(RN)1 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.

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