Synthesis of 1,3-diarylated imidazo[1,5-a]pyridines with a combinatorial approach: metal-catalyzed cross-coupling reactions of 1-halo-3-arylimidazo[1,5-a]pyridines with arylmetal reagents
Synthesis of 1,3-diarylated imidazo[1,5-a]pyridines with a combinatorial approach: metal-catalyzed cross-coupling reactions of 1-halo-3-arylimidazo[1,5-a]pyridines with arylmetal reagents
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DOI：
10.1016/j.tet.2009.02.062
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发表时间：
2009-06-27
期刊：
影响因子：
2.1
通讯作者：
Murai, Toshiaki
中科院分区：
文献类型：
--
作者：
Shibahara, Fumitoshi;Yamaguchi, Eiji;Murai, Toshiaki
以碘、溴、N-氯代丁二酰亚胺和1-氟-2，4，6-三甲基吡啶四氟硼酸盐为卤化剂，对3-芳基咪唑并[1，5-a]吡啶进行卤代反应，得到了选择性卤代产物1-卤代-3-芳基咪唑并[1，5-a]吡啶。所得1-碘-3-芳基咪唑并[1，5-a]吡啶与芳基Grignard试剂的Kumada-Tamao-Corriu交叉偶联导致1，3-二芳基咪唑并[1，5-a]吡啶的良好至优异的产率。1-溴-3-苯基咪唑并[1，5-a]吡啶与对-或间-甲氧羰基苯基硼酸的Suzuki-Miyaura交叉偶联分别以91%和61%的产率提供偶联产物。所得的1，3-二芳基咪唑并[1，5-a]吡啶在449-533 nm波长范围内显示出多种荧光发射，与单芳基咪唑并[1，5-a]吡啶相比，量子产率有所提高。(C)2009爱思唯尔有限公司版权所有。
The halogenation of 3-arylimidazo[1,5-a]pyridines was carried out with iodine, bromine, N-chlorosuccinimide, and 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate as halogenating agents to give selectively halogenated products 1-halo-3-arylimidazo[1,5-a]pyridines in good to excellent yields. Kumada-Tamao-Corriu cross-coupling of the obtained 1-iodo-3-arylimidazo[1,5-a]pyridines and aryl Grignard reagents led to 1,3-diarylated imidazo[1,5-a]pyridines in good to excellent yields. Suzuki-Miyaura cross-coupling of the 1-bromo-3-phenylimidazo[1,5-a]pyridine and p- or m-methoxycarbonylphenylboronic acids furnished the coupling product in respective yields of 91% and 61%. The obtained 1,3-diarylated imidazo[1,5-a]pyridines showed a wide variety of fluorescent emissions in a wavelength range of 449-533 nm with improved quantum yields compared to monoarylated ones. (C) 2009 Elsevier Ltd. All rights reserved.