Dj. Ramon et M. Yus, CARBAMOYL AND THIOCARBAMOYL LITHIUM - A NEW ROUTE BY NAPHTHALENE-CATALYZED CHLORINE-LITHIUM EXCHANGE, Tetrahedron letters, 34(44), 1993, pp. 7115-7118
The reaction of N,N-diisopropylcarbamoyl or N,N-dimethylthiocarbamoyl
chloride (1a or 1b) with an excess of lithium powder and a catalytic a
mount of naphthalene (3 mol %) in the presence of a carbonyl compound
2 at temperatures ranging between -78 and 20-degrees-C, under Barbier-
type conditions leads, after hydrolysis with water, to the correspondi
ng alpha-hydroxy amides or thioamides 3, respectively.