Preparation of Polyfunctional Organozinc Halides by an InX3- and LiCl-Catalyzed Zinc Insertion to Aryl and Heteroaryl Iodides and Bromides

被引：13

作者：

Benischke, Andreas D. ^{[1
]}

Le Corre, Gregoire ^{[2
]}

Knochel, Paul ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany

[2] Ecole Polytech, CNRS, Lab Chim Mol, Route Saclay, F-91128 Palaiseau, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 04期

关键词：

cross-coupling; indium; lithium chloride; organozinc reagents; zinc; NEGISHI CROSS-COUPLINGS; CARBON BOND FORMATION; FUNCTIONALIZED ARYLZINC; UNSATURATED HALIDES; ORGANOMAGNESIUM REAGENTS; 1,2-DIMETALLIC COMPOUNDS; ORGANOMETALLIC REAGENTS; OXIDATIVE ADDITION; GRIGNARD-REAGENTS; ORGANIC HALIDES;

D O I：

10.1002/chem.201605139

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic system consisting of InCl3 (3 mol%) and LiCl (30 mol%) allows a convenient preparation of polyfunctional arylzinc halides via the insertion of zinc powder to various aryl iodides in THF at 50 degrees C in up to 95% yield. The use of a THF/DMPU (1: 1) mixture shortens the reaction rates and allows the preparation of keto-substituted arylzinc reagents. In the presence of In(acac)(3) (3 mol%) and LiCl (150 mol%), the zinc insertion to various aryl and heteroaryl bromides proceeds smoothly (50 degrees C, 2-18 h). Alkyl bromides are also converted to the corresponding zinc reagents in the presence of In(acac)(3) (10 mol%) and LiCl (150 mol%) in 70-80% yield.

引用

页码：778 / 782

页数：5

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