Development of an Air-Stable, Broadly Applicable Nickel Source for Nickel-Catalyzed Cross-Coupling

被引:106
作者
Magano, Javier [1 ]
Monfette, Sebastien [1 ]
机构
[1] Pfizer Inc, Worldwide Res & Dev, Groton, CT 06340 USA
关键词
cross-coupling; nickel; precatalyst; air stability; homogeneous catalysis; ARYL CHLORIDES; PRECATALYST; BROMIDES; HALIDES; LIGAND;
D O I
10.1021/acscatal.5b00498
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The synthesis of NiCl(o-tolyl)(TMEDA) (3; TMEDA = tetramethylethylenediamine) and its application in coupling reactions is described. In combination with a suitable ligand, precatalyst 3 was applied to a wide range of transformations, such as Suzuki, amination, Kumada, Negishi, Heck, borylation, and reductive coupling. Yields of products obtained with 3 are equal or superior to those obtained with common Ni sources such as Ni(cod)(2) (1) and NiCl2(dme) (2). Importantly, and unlike 1, complex 3 is stable for months in air as a solid, which eliminates the need for a glovebox and greatly facilitates the reaction setup. Thus, complex 3 is the first highly versatile Ni source that combines the broad applicability of 1 with the air stability of 2.
引用
收藏
页码:3120 / 3123
页数:4
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