Defluorophosphorylation of fluoroalkyl peroxides for the synthesis of highly substituted furans

被引：13

作者：

Chu, Xue-Qiang ^{[1
]}

Cai, Song-Zhou ^{[1
]}

Chen, Jia-Wei ^{[1
]}

Yu, Zi-Lun ^{[1
]}

Ma, Mengtao ^{[3
]}

Walsh, Patrick J. ^{[2
]}

Shen, Zhi-Liang ^{[1
]}

机构：

[1] Nanjing Tech Univ, Tech Inst Fluorochemistry TIF, Inst Adv Synth, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China

[2] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, 231 South 34th St, Philadelphia, PA 19104 USA

[3] Nanjing Forestry Univ, Coll Sci, Dept Chem & Mat Sci, Nanjing 210037, Peoples R China

来源：

GREEN CHEMISTRY | 2023年 / 25卷 / 05期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

P BOND FORMATION; C-O; ARYL; PHOSPHORYLATION; ANNULATION; PHOSPHONATION; CONSTRUCTION; PHOSPHINES; STRATEGY; LIGANDS;

D O I：

10.1039/d2gc04512e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 formation in two reaction modes.

引用

页码：2000 / 2010

页数：11

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