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
收藏
页码：778 / 782
页数：5
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