Highly Chemoselective Reduction of Phosphine Oxides through Electrophilic Activation of the P=O Bond with Anhydride

Author:

Jin Hongyu1,Gu Chengshan1,Xiao Zhihuan1,Tan Qihang1,Liu Long1,Han Li‐Biao2ORCID,Chen Wen‐Hao3,Chen Tieqiao1ORCID

Affiliation:

1. Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources Hainan Provincial Key Lab of Fine Chem Hainan Provincial Fine Chemical Engineering Research Center College of Chemical Engineering and Technology Hainan University Haikou 570228 P. R. China

2. Zhejiang Yangfan New Materials Co. Ltd. Shangyu 312369 P. R. China

3. Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education College of Chemistry and Chemical Engineering Hainan Normal University Haikou 571158 P. R. China

Abstract

AbstractA highly chemoselective reduction of phosphine oxides was demonstrated under transition‐metal‐free and alkaline reaction conditions. During the reaction, P=O bond was firstly electrophilically activated by an anhydride and subsequently reduced by the versatile and cheap NaH, which was strengthened by 15‐crown‐5. By this strategy, a variety of phosphine oxides including those bearing functional groups such as methyl, methoxyl, phenyl, fluorine, chlorine, bromine, iodine, trifluoromethyl, nitrile, ester, alkenyl, alkynyl and heterocycles were transformed readily into the corresponding phosphines in good to high yields. This work represents an efficient method for reducing phosphine oxides forming phosphines.

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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