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

页码：4967 / 4971

页数：5

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