Azobisisobutyronitrile-Initiated Oxidative C-H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[ b]phosphole Oxides and 6 H-Indeno[2,1- b]phosphindole 5-Oxide Derivatives

Jiami Guo; Chenlu Mao; Bin Deng; Liyi Ye; Yingwu Yin; Yuxing Gao; Song Tu

doi:10.1021/acs.joc.0c00118

Azobisisobutyronitrile-Initiated Oxidative C-H Functionalization of Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free Approach toward Hydroxymethyl Benzo[ b]phosphole Oxides and 6 H-Indeno[2,1- b]phosphindole 5-Oxide Derivatives

J Org Chem. 2020 May 15;85(10):6359-6371. doi: 10.1021/acs.joc.0c00118. Epub 2020 Apr 23.

Authors

Jiami Guo¹, Chenlu Mao¹, Bin Deng¹, Liyi Ye¹, Yingwu Yin¹, Yuxing Gao², Song Tu¹

Affiliations

¹ Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China.
² Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, China.

PMID: 32299209
DOI: 10.1021/acs.joc.0c00118

Abstract

The first metal-free and facile radical addition/cyclization of simple alcohols with diaryl(arylethynyl)phosphine oxides has been described with azobisisobutyronitrile as a radical initiator, affording an efficient and one-pot procedure to access a new class of hydroxymethyl benzo[b]phosphole oxides and 6H-indeno[2,1-b]phosphindole 5-oxides for potential application in organic materials via sequential C(sp³)-H/C(sp²)-H functionalization. The method employs easily accessible starting materials and is endowed with high regioselectivity and broad functional-group tolerance.