Organometallic control over the regiospecificity of functionalization reactions: 1,2,3-trifluorobenzene and bromo derivatives thereof as substrates

被引：43

作者：

Heiss, C

Schlosser, M ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Inst Chim Mol & Biol, BCh, CH-1015 Lausanne, Switzerland

[2] Univ Lausanne, Fac Sci, BCh, CH-1015 Lausanne, Switzerland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 03期

关键词：

halogen-metal permutation; halogen migration; metalations; neighboring group assistance; regioselectivity;

D O I：

10.1002/ejoc.200390078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In a case study, 1,2,3-trifluorobenzene was functionalized at each of the two vacant positions (producing the benzoic acids 1 and 2) and, in addition, bromine was introduced into all available positions (producing the benzoic acids 3-5). The required regioflexibility was achieved by applying novel organometallic recipes such as deprotonation-triggered halogen migrations and site-discriminating competitive halogen-metal permutations.

引用

页码：447 / 451

页数：5

共 19 条

[1]

Bobbio C, 2001, EUR J ORG CHEM, V2001, P4533

[2] Additivity of substituent effects in the fluoroarene series: Equilibrium acidity in the gas phase and deprotonation rates in ethereal solution [J].