Addition of Grignard reagents to nitriles to give ketones (after hydrolysis)
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2. a. Effet du benzene dans la reaction de Grignard sur les nitriles
Persephone Canonne, George B.Foscolos, Gilles Lema Tetrahedron Letters 1980, 155 DOI: 10.1016/S0040-4039(00)71400-6
Use of benzene containing one equivalent of ether as solvent in Grignard reactions of nitriles at room temperature leads to increased yields of the corresponding ketones compared to results obtained for the same reactions in ether.
b. Organometallic reaction mechanisms. XII. Mechanism of methylmagnesium bromide addition to benzonitrile
E. C. Ashby, Li-Chung. Chao, and H. M. Neumann Journal of the American Chemical Society 1973 95 (15), 4896-4904 DOI: 10.1021/ja00796a022
The kinetic data of the title reaction show a second-order reaction, first order in Grignard reagent and first order in nitrile. The results of rate studies in the presence of added MgBr2 show that the reaction of the Grignard reagent with benzonitrile occurs through both the (CH3)2Mg and CH3MgBr species.
c. The Mechanism of Addition of Grignard Reagents to Nitriles
C. Gardner Swain Journal of The American Chemical Society, 1947, 69(10), 2306 DOI: 10.1021/ja01202a018
This paper is an early literature reference to this reaction and describes a kinetic study of the reaction between n-butylmagnesium bromide and benzonitrile, which was found to be 2nd order.
3. Copper(I)-activated addition of Grignard reagents to nitriles. Synthesis of ketimines, ketones, and amines
Franz J. Weiberth and Stan S. Hall The Journal of Organic Chemistry 1987 52 (17), 3901-390 DOI: 10.1021/jo00226a033
The nucleophilic addition of Grignard reagents to nitriles, especially when using sterically demanding components, is effectively catalyzed by copper(I) salts.
4. Pearson-Long, M. S. M., Boeda, F., & Bertus, P. (2016).
Double Addition of Organometallics to Nitriles: Toward an Access to Tertiary Carbinamines. Advanced Synthesis & Catalysis, 359(2), 179–201 DOI: 10.1002/adsc.201600727
This review describes a variant of this reaction – the double addition of organometallics (e.g. Grignard reagents or organolithium reagents) to nitriles.