Tetrahedron p. 3447 - 3452 (1994)
Update date:2022-08-17
Topics:
Guijarro
Yus
The reaction of different nitriles 1 with an excess of lithium powder (1:14 molar ratio) and a catalytic amount of 4,4'-di-tert-butylbiphenyl (5 mol %) in the presence of a carbonyl compound (Barbier-type conditions) in THF at low temperature (-30 or -78°C) leads to the corresponding compounds 2 resulting from the coupling between the electrophile and the organolithium intermediate arising from a reductive decyanation of the starting nitrile 1. This new reaction can be also applied to the use of trimethylchlorosilane as electrophile at 0°C.
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