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Surprising and Highly Efficient Use of Methylmagnesium Chloride as a Non‐Nucleophilic Base in the Deprotonation and Alkylation of sp 3 Centres Adjacent to Nitriles
Author(s) -
Gbadebo Omolola,
Smith Dennis,
Harnett Ger,
Donegan Gregory,
O'Leary Patrick
Publication year - 2018
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.201801462
Subject(s) - chemistry , deprotonation , alkylation , nucleophile , nitrile , reagent , base (topology) , amine gas treating , combinatorial chemistry , chloride , organic chemistry , catalysis , ion , mathematical analysis , mathematics
Methylmagnesium chloride (MeMgCl) is a key reagent in research and industry typically as a nucleophile. In this article we develop the use of MeMgCl as a non‐nucleophilic base in conjunction with catalytic amounts of an amine mediator. Specifically, we use the base to deprotonate α to a variety of nitriles in alkylation reactions, applying it to the synthesis of a wide variety of tertiary and quaternary nitriles, including examples where we successively and successfully added three different substituents on the carbon α to the nitrile. This method is generally applicable, high yielding and much greener than existing methods, and it has considerable advantages for industrial application.