Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: regioselective synthesis of heteroarylboronates
Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: regioselective synthesis of heteroarylboronates
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DOI：
10.1016/s0040-4039(02)01135-8
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发表时间：
2002-08-05
影响因子：
1.8
通讯作者：
Miyaura, N
中科院分区：
文献类型：
--
作者：
Takagi, J;Sato, K;Miyaura, N
在1/2-[IrCl（COD）]（2）-（4，4 ′-二叔丁基-2，2 ′-联吡啶）催化剂（3mol%）存在下，于80 ~ 100 ℃在正辛烷中进行了芳香杂环与二硼频哪醇酯的C-H偶联反应。噻吩、呋喃、吡咯及其苯并稠合衍生物等五元底物的反应只产生2-硼基化产物，而吡啶和喹啉等六元杂环的反应则选择性地发生在3-位。通过使用几乎等摩尔量的底物和二硼，也实现了双（硼基）杂芳族化合物的区域选择性合成。(C)2002爱思唯尔科技有限公司版权所有。
The C-H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80 100degreesC in the presence of a 1/2-[IrCl(COD)](2)-(4,4'-di-tert-butyl-2,2'-bipyridine)catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively occurred at the 3-position. Regioselective synthesis of bis(boryl)heteroaromaties was also achieved by using an almost equimolar amount of substrates and the diboron. (C) 2002 Elsevier Science Ltd. All rights reserved.