Non-Cryogenic CeCl₃-Promoted Double Additions of Methyllithium and n-Butyllithium to Unsaturated Nitriles

Abstract

Subjection of methyl or n-butyllithium to a mixture of nitriles and activated cerium chloride in THF at -10 to 0 °C afforded the corresponding carbinamines, which were isolated as either the hydrochloride salts or acetamide or benzamide derivatives in 30-91% yields.

Key words

carbinamines - carbinamides - organocerium reagents - non-cryogenic conditions - reaction optimization

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11

For a previous report on reaction between ketone-CeCl₃ complexes and Grignard reagents at 0 °C, see ref. 3a.

12

Anhyd CeCl₃ for these studies was obtained from GFS Chemicals at $ 1.06/gram.