Defluorophosphorylation of Fluoroalkyl Peroxides for the Synthesis of Highly Substituted Furans

Xue-Qiang Chu,*^,a Song-Zhou Cai (蔡松州),^a Jia-Wei Chen,^a Zi-Lun Yu,^a Mengtao Ma,^c Patrick J. Walsh,*^,b and Zhi-Liang Shen*^,a

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

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

^c Department 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 and C4-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.

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

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