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

Hong-Chen Li; 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

doi:10.1021/acs.orglett.8b02244

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

Org Lett. 2018 Sep 21;20(18):5573-5577. doi: 10.1021/acs.orglett.8b02244. Epub 2018 Aug 29.

Authors

Affiliations

¹ College of Chemistry and Materials Engineering , Wenzhou University , Wenzhou 325035 , People's Republic of China.
² School of Pharmaceutical Science , Wenzhou Medical University , Wenzhou 325035 , People's Republic of China.

PMID: 30156855
DOI: 10.1021/acs.orglett.8b02244

Abstract

A novel metal-free reduction system, in which H₂Se (or HSe^-) produced in situ from Se/DMF/H₂O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H₂O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation.

Publication types

Research Support, Non-U.S. Gov't