Visible-Light-Induced Oxidative C-H Functionalization of Unreactive Cycloalkanes, Alcohols, and Ethers with Alkynylphosphine Oxides into Benzo[ b]phosphole Oxides under Photocatalyst-, Metal-, and Base-Free Conditions

Baffa Haruna; Weitu Hong; Warsame Ibrahim Mohamed; Jiami Guo; Liyi Ye; Yingwu Yin; Yuxing Gao; Song Tu

doi:10.1021/acs.joc.1c00841

Visible-Light-Induced Oxidative C-H Functionalization of Unreactive Cycloalkanes, Alcohols, and Ethers with Alkynylphosphine Oxides into Benzo[ b]phosphole Oxides under Photocatalyst-, Metal-, and Base-Free Conditions

J Org Chem. 2021 Sep 17;86(18):13092-13099. doi: 10.1021/acs.joc.1c00841. Epub 2021 Sep 1.

Authors

Baffa Haruna¹, Weitu Hong¹, Warsame Ibrahim Mohamed¹, Jiami Guo¹, 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: 34470208
DOI: 10.1021/acs.joc.1c00841

Abstract

We developed the radical cyclization/addition of alkynylphosphine oxides with easily available cycloalkanes, alcohols, and ethers using a visible-light and environmentally friendly synthetic strategy in the absence of photocatalyst at room temperature. This mild and metal- and base-free reaction provided a structurally varied set of significant benzo[b]phosphole oxides through sequential C-H functionalization in an atom-economical manner.