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Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia

Liping Cao, Jiaoyang Ding, Meng Gao, Zihua Wang, Juan Li and Anxin Wu*

*Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. China, Email: chwuaxmail.ccnu.edu.cn

L. Cao, J. Ding, M. Gao, Z. Wang, J. Li, A. Wu, Org. Lett., 2009, 11, 3810-3813.

DOI: 10.1021/ol901250c (free Supporting Information)


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Abstract

An iodine-NH3 • H2O system enables a direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to the corresponding primary amides in good yields in aqueous media. A tandem Lieben-Haller-Bauer reaction mechanism is proposed.

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proposed reaction pathway



Key Words

Lieben Haloform Reaction, Haller-Bauer Reaction, Amides (Amidation, Oxidation), Iodine


ID: J54-Y2009-2590