Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence

被引：35
|
作者：
Kikuchi, Takao [1 ]
Nobuta, Yusuke [1 ]
Umeda, Junko [1 ]
Yamamoto, Yasunori [1 ]
Ishiyama, Tatsuo [1 ]
Miyaura, Norio [1 ]
机构：
[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan
来源：
TETRAHEDRON | 2008年 / 64卷 / 22期
关键词：
pinacolborane; biaryls; boron; C-H activation; cross-coupling;
D O I：
10.1016/j.tet.2008.03.102
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C-H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)](2)-(4,4'-di-tert-butyl-2,2'-bipyridine) at 25 degrees C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 degrees C in the presence of PdCl(2)(dppf) (3.0 mol %) and K(3)PO(4) in DMF. This one-pot, two-step procedure provided a variety of unsymmetrical biaryls in high yields. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4967 / 4971
页数：5
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