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Regioselective Hydration of Terminal Alkynes Catalyzed by a Neutral Gold(I) Complex [(IPr)AuCl] and One-Pot Synthesis of Optically Active Secondary Alcohols from Terminal Alkynes by the Combination of [(IPr)AuCl] and Cp*RhCl[(R,R)-TsDPEN]

Feng Li*, Nana Wang, Lei Lu and Guangjun Zhu

*Key Laboratory for Soft Chemistry and Functional Materials, Ministry of Education, Nanjing University of Science & Technology, Nanjing 210094, People’s Republic of China, Email: fenglinjust.edu.cn

F. Li, N. Wang, L. Lu, G. Zhu, J. Org. Chem., 2015, 80, 3538-3546.

DOI: 10.1021/acs.joc.5b00164 (free Supporting Information)


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Abstract

The neutral gold(I) complex [(IPr)AuCl] is a highly effective catalyst for the regioselective hydration of terminal alkynes, including aromatic alkynes and aliphatic alkynes providing methyl ketones in high yields. Furthermore, optically active alcohols could be obtained in high yields with very good enatioselectivities via one-pot sequential hydration/asymmetric transfer hydrogenation using Cp*RhCl[(R,R)-TsDPEN] as additional catalyst.

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Key Words

hydration of alkynes, benzyl alcohols, sodium formate


ID: J42-Y2015