Selective P-C(sp3 ) Bond Cleavage and Radical Alkynylation of α-Phosphorus Alcohols by Photoredox Catalysis

Kunfang Jia; Junzhao Li; Yiyun Chen

doi:10.1002/chem.201800202

Selective P-C(sp³ ) Bond Cleavage and Radical Alkynylation of α-Phosphorus Alcohols by Photoredox Catalysis

Chemistry. 2018 Mar 2;24(13):3174-3177. doi: 10.1002/chem.201800202. Epub 2018 Feb 5.

Authors

Kunfang Jia¹, Junzhao Li¹, Yiyun Chen¹

Affiliation

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.

PMID: 29356137
DOI: 10.1002/chem.201800202

Abstract

Herein the first P-C(sp³ ) bond cleavage and radical alkynylation of α-phosphorus alcohols to construct phosphonoalkynes is reported. The phosphorus radical is generated upon P-C bond cleavage reaction via the alkoxyl radical through photoredox catalysis with cyclic iodine(III) reagents. Various arylphosphinoyl-, alkylphosphinoyl-, phosphonate-, and phosphonic amide alcohols serve as radical phosphorus precursors to construct phosphonoalkynes for the first time.

Keywords: P−C(sp3) bond cleavage; alkynylation; phosphorus; photochemistry; radicals.