Synthesis 2006(24): 4143-4150  
DOI: 10.1055/s-2006-950362
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

John Limanto*, Benjamin Dorner, Paul N. Devine
Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, NJ 07065, USA
Fax: +1(732)5941499; e-Mail: john_limanto@merck.com;
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Publikationsverlauf

Received 18 August 2006
Publikationsdatum:
14. November 2006 (online)

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.

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.