Copper-Catalyzed Aza-Michael Addition of Aromatic Amines or Aromatic Aza-Heterocycles to α,β-Unsaturated Olefins

Seongcheol Kim, Seongil Kang, Gihyeon Kim and Yunmi Lee*

*Department of Chemistry, Kwangwoon University, Seoul 01897, Republic Korea, Email: ymleekw.ac.kr

S. Kim, S. Kang, G. Kim, Y. Lee, J. Org. Chem., 2016, 81, 4048-4057.

DOI: 10.1021/acs.joc.6b00341

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Abstract

A highly efficient and mild conjugate addition reaction of aromatic amines and aromatic aza-heterocycles to α,β-unsaturated olefins is promoted by 3-7 mol % of a Cu complex generated in situ from a mixture of inexpensive CuCl, a readily available phosphine or imidazolium salt, and KOtBu at ambient temperature. A wide range of β-amino sulfone, β-amino nitrile, and β-amino carbonyl compounds is selectively synthesized in high yields.

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Key Words

Michael Addition, β-Amino ketones and nitriles

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ID: J42-Y2016