Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H₂O System

Cui An, Ge Wu, Guo-Xing Li, Xiao-Bo Huang, Wen-Xia Gao, Jin-Chang Ding, Yun-Bing Zhou*, Miao-Chang Liu*, Hua-Yue Wu

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China, Email: zybwzu.edu.cn, mclwzu.edu.cn

C. An, G. Wu, G.-X. Li, X.-B. Huang, W.X. Gao, J.-C. Ding, Y.-B. Zhou, M.-C. Liu, H.-Y. Wu, Org. Lett., 2018, 20, 5573-5577.

DOI: 10.1021/acs.orglett.8b02244

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Abstract

H₂Se (or HSe^-) produced in situ from Se/DMF/H₂O is an active reducing species. This reduction system with water as an inexpensive, safe, and environmentally friendly hydrogen donor displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes.

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proposed reaction pathway

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Key Words

1,4-reduction, semireduction of alkynes, selenium

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ID: J54-Y2018