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Highly Practical Synthesis of Nitriles and Heterocycles from Alcohols under Mild Conditions by Aerobic Double Dehydrogenative Catalysis

Weiyu Yin, Chengming Wang and Yong Huang*

*Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, China, India, Email: huangyongpkusz.edu.cn

W. Yin, C. Wang, H. Huang, Org. Lett., 2013, 15, 1850-1853.

DOI: 10.1021/ol400459y (free Supporting Information)


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Abstract

A mild, aerobic, catalytic synthesis of nitriles directly from alcohols and aqueous ammonia proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of oxygen. The substrate scope includes various functionalized aromatic and aliphatic alcohols. This protocol also enabled a one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.

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Key Words

nitriles, oxygen, TEMPO


ID: J54-Y2013