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Manganese‐Catalyzed Aerobic Heterocoupling of Aryl Grignard Reagents
Author(s) -
Ghaleshahi Hajar Golshahi,
Antonacci Giuseppe,
Madsen Robert
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700007
Subject(s) - chemistry , reagent , aryl , catalysis , grignard reagent , grignard reaction , coupling reaction , manganese , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl
An improved protocol has been developed for the MnCl 2 ‐catalyzed cross‐coupling reaction of two arylmagnesium bromides under dioxygen. The reaction was achieved by using the Grignard reagents in a 2:1 ratio and 20 % of MnCl 2 . Very good yields of the heterocoupling product were obtained when the limiting Grignard reagent underwent little homocoupling under the reaction conditions. Arylmagnesium bromides that contain p ‐methoxy, p ‐(dimethylamino), p ‐fluoro, and p ‐chloro substituents were shown to afford high product yields in the cross‐coupling reactions with a variety of substituted aryl Grignard reagents. Heterocyclic Grignard reagents, on the other hand, were less effective substrates for this transformation because of the rapid homocoupling of these reagents under the reaction conditions.