Phosphinoyl-functionalization of unactivated alkenes through phosphinoyl radical-triggered distal functional group migration

被引：56

作者：

Chen, Dong ^{[1
]}

Wu, Zhen ^{[1
]}

Yao, Yingming ^{[1
]}

Zhu, Chen ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, 199 Ren Ai Rd, Suzhou 215123, Jiangsu, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 15期

基金：

中国国家自然科学基金;

关键词：

VISIBLE-LIGHT PHOTOCATALYSIS; C BOND FORMATION; CROSS-COUPLING REACTIONS; METAL-FREE; H FUNCTIONALIZATION; CATALYZED PHOSPHORYLATION; STEREOSELECTIVE-SYNTHESIS; DIARYLPHOSPHINE OXIDES; PHOTOREDOX CATALYSIS; PHOSPHORUS LIGANDS;

D O I：

10.1039/c8qo00558c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Disclosed herein is a novel and practical protocol for the radical-mediated phosphinoyl-functionalization of unactivated alkenes. The P-centered radicals are generated in the presence of TBHP under mild reaction conditions, which trigger the subsequent distal functional group migration. Both phosphine oxides and phosphonates are suitable precursors for the delivery of phosphinoyl radicals. As a result, phosphinoyl radicals along with another functional group such as heteroaryl, cyano, or imino are incorporated to alkenes concurrently. A wide range of synthetically valuable alkylphosphorus compounds are furnished in good yields.

引用

页码：2370 / 2374

页数：5

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