Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions

被引:545
作者
Bruno, Nicholas C. [1 ]
Tudge, Matthew T. [2 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
[2] Merck & Co Inc, Global Chem, Rahway, NJ 07065 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
SUZUKI-MIYAURA; PRIMARY AMINES; AMINATION; CYCLOPALLADATION; PHOSPHINES; COMPLEXES; CATALYSTS; REAGENTS;
D O I
10.1039/c2sc20903a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of easily prepared, phosphine-ligated palladium precatalysts based on the 2-aminobiphenyl scaffold have been prepared. The role of the precatalyst-associated labile halide (or pseudohalide) in the formation and stability of the palladacycle has been examined. It was found that replacing the chloride in the previous version of the precatalyst with a mesylate leads to a new class of precatalysts with improved solution stability and that are readily prepared from a wider range of phosphine ligands. The differences between the previous version of precatalyst and that reported here are explored. In addition, the reactivity of the latter is examined in a range of C-C and C-N bond forming reactions.
引用
收藏
页码:916 / 920
页数:5
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