Cobalt-Catalyzed Negishi Cross-Coupling Reactions of (Hetero)Arylzinc Reagents with Primary and Secondary Alkyl Bromides and Iodides

被引：77
|
作者：
Hammann, Jeffrey M. [1 ]
Haas, Diana [1 ]
Knochel, Paul [1 ]
机构：
[1] Univ Munich, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 15期
关键词：
cobalt; cross-coupling; heterocycles; metalation; zinc; DIRECTED ORTHO-METALATION; ARYL GRIGNARD-REAGENTS; CENTER-DOT-LICL; 6-HALO-1-HEXENE DERIVATIVES; CHEMOSELECTIVE METALATION; HALIDES; ZINCATION; AMIDE; BASE; FUNCTIONALIZATION;
D O I：
10.1002/anie.201411960
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report a cobalt-catalyzed cross-coupling of di(hetero)arylzinc reagents with primary and secondary alkyl iodides or bromides using THF-soluble CoCl(2)2LiCl and TMEDA as a ligand, which leads to the corresponding alkylated products in up to 88% yield. A range of functional groups (e.g. COOR, CN, CF3, F) are tolerated in these substitution reactions. Remarkably, we do not observe rearrangement of secondary alkyl iodides to unbranched products. Additionally, the use of cyclic TBS-protected iodohydrins leads to trans-2-arylcyclohexanol derivatives in excellent diastereoselectivities (up to d.r.=99:1).
引用
收藏
页码：4478 / 4481
页数：4
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