Rhodium(III)-Catalyzed Direct Coupling of Arylphosphine Derivatives with Heterobicyclic Alkenes: A Concise Route to Biarylphosphines and Dibenzophosphole Derivatives

被引：93

作者：

Unoh, Yuto ^{[1
,2
]}

Satoh, Tetsuya ^{[1
,2
,3
]}

Hirano, Koji ^{[1
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] JST, ACT C, Kawaguchi, Saitama 3320012, Japan

[3] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, Osaka 5588585, Japan

来源：

ACS CATALYSIS | 2015年 / 5卷 / 11期

关键词：

rhodium; phosphine; phosphole; heterobicyclic alkene; C-H bond functionalization; arylation; H BOND FUNCTIONALIZATIONS; PALLADIUM(II)-CATALYZED ORTHO-OLEFINATION; PALLADIUM-CATALYZED SYNTHESIS; ARYL HYDROGEN PHOSPHATES; FRIEDEL-CRAFTS REACTION; C-H; ORTHO-ARYLATION; ORTHO-ALKENYLATION; ACTIVATION; LIGANDS;

D O I：

10.1021/acscatal.5b01896

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The redox-neutral direct coupling of arylphosphine oxides with heterobicyclic alkenes proceeds smoothly under rhodium(III) catalysis involving hydroarylation followed by dehydrative aromatization to form biarylphosphine oxides. Related phenylphosphinic and phenylphosphonic esters as well as phenylphosphine sulfides also undergo ortho-arylative coupling. Furthermore, phenylphosphinothioic amides can be transformed to fused dibenzophosphole derivatives through rhodium-catalyzed coupling with heterobicyclic alkenes and successive intramolecular phospha-Friedel Crafts reaction in a one-pot manner.

引用

页码：6634 / 6639

页数：6

共 109 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].