Iron and Manganese Catalysts for the Selective Functionalization of Arene C(sp2)-H Bonds by Carbene Insertion

被引：68

作者：

Conde, Ana ^{[1
]}

Sabenya, Gerard ^{[2
,3
]}

Rodriguez, Monica ^{[2
,3
]}

Postils, Veronica ^{[2
,3
]}

Luis, Josep M. ^{[2
,3
]}

Diaz-Requejo, M. Mar ^{[1
]}

Costas, Miquel ^{[2
,3
]}

Perez, Pedro J. ^{[1
]}

机构：

[1] Univ Huelva, CIQSO Ctr Invest Quim Sostenible, Lab Catalisis Homogenea, Unidad Asociada CSIC,Dept Quim, Campus El Carmen S-N, Huelva 21007, Spain

[2] Univ Girona, IQCC, Campus Montilivi, Girona 17071, Spain

[3] Univ Girona, Dept Quim, Campus Montilivi, Girona 17071, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 22期

关键词：

arenes; carbene; C-H activation; iron; manganese; ALPHA-DIAZOCARBONYL COMPOUNDS; C-H FUNCTIONALIZATION; DIAZO-COMPOUNDS; ETHYL DIAZOACETATE; ORGANIC-SYNTHESIS; BUCHNER REACTION; GOLD CATALYSIS; ACTIVATION; COMPLEXES; OXIDATION;

D O I：

10.1002/anie.201601750

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first examples of the direct functionalization of non-activated aryl sp(2) C-H bonds with ethyl diazoacetate (N2CHCO2Et) catalyzed by Mn- or Fe-based complexes in a completely selective manner are reported, with no formation of the frequently observed cycloheptatriene derivatives through competing Buchner reaction. The best catalysts are Fe-II or Mn-II complexes bearing the tetradentate pytacn ligand (pytacn = 1-(2-pyridylmethyl)-4,7-dimethyl-1,4,7-triazacyclononane). When using alkylbenzenes, the alkylic C(sp(3))-H bonds of the substituents remained unmodified, thus the reaction being also selective toward functionalization of sp(2) C-H bonds.

引用

页码：6530 / 6534

页数：5

共 50 条

[1] TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .2. ADDITION TO AROMATIC-MOLECULES - CATALYSIS OF BUCHNER SYNTHESIS OF CYCLOHEPTATRIENES [J].