Defluorophosphorylation of Fluoroalkyl Peroxides for the Synthesis of Highly Substituted Furans

Xue-Qiang Chu,*^,aSong-Zhou Cai(蔡松州),^aJia-Wei Chen,^aZi-Lun Yu,^aMengtao Ma,^cPatrick J. Walsh,*^,band Zhi-Liang Shen*^,a

^aTechnical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

^bRoy and Diana Vagelos Laboratories, Department of Chemistry University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.

^cDepartment of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, China.

Abstract:Transformation of multifunctional materials with control over site-selectivity and chemical diversity remains challenging. Herein, we present a metal-free, one-pot strategy for the defluorophosphorylation of polyfluoroalkyl peroxides that enables expedient construction of structurally diverse phosphoryl-containing heterocyclic libraries. By judicious choice of reaction conditions,C3,4-diphosphoryl furans andC4-monophosphoryl furans can be easily accessed. In addition, synthetic derivatization of the obtained organophosphorus heteroarenes to value-added monodentate and bidentate phosphines has been demonstrated. Mechanistic studies revealed that regioselective defluorophosphorylation allows divergent product formations in two reaction modes.

GreenChem.2023, DOI:10.1039/D2GC04512E.(Impact factor:11.034)

论文链接：https://doi.org/10.1039/D2GC04512E.