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Substrate Controlled Regioselective Bromination of Acylated Pyrroles Using Tetrabutylammonium Tribromide (TBABr3)
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-07-03 00:00:00 , DOI: 10.1021/acs.joc.8b01251
Shuang Gao 1 , Travis K. Bethel 1 , Tayeb Kakeshpour 1 , Grace E. Hubbell 1 , James E. Jackson 1 , Jetze J. Tepe 1
Affiliation  

Electrophilic bromination of pyrroles bearing carbonyl substituents at C-2 typically results in a mixture of the 4- and 5-brominated species, generally favoring the 4-position. Herein, we describe a substrate-controlled regioselective bromination in which tetra-butyl ammonium tribromide (TBABr3) reacts with pyrrole-2-carboxamide substrates to yield the 5-brominated species as the predominant (up to >10:1) product.

中文翻译:

使用三丁基四溴化铵(TBABr 3)的底物控制的酰化吡咯的区域选择性溴化反应

在C-2处带有羰基取代基的吡咯的亲电溴化反应通常会产生4-溴和5-溴化物质的混合物,通常有利于4-位。在本文中,我们描述了受底物控制的区域选择性溴化反应,其中四丁基三溴化铵(TBABr 3)与吡咯-2-羧酰胺底物反应,生成以5溴化物为主的(高达> 10:1)产物。
更新日期:2018-07-03
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