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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:,

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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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

Key Words

1,4-reduction, semireduction of alkynes, selenium

ID: J54-Y2018