METAL-HALOGEN EXCHANGE OF BROMOINDOLES - A ROUTE TO SUBSTITUTED INDOLES
METAL-HALOGEN EXCHANGE OF BROMOINDOLES - A ROUTE TO SUBSTITUTED INDOLES
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DOI：
10.1021/jo00376a010
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发表时间：
1986-12-26
影响因子：
3.6
通讯作者：
RAPOPORT, H
中科院分区：
文献类型：
--
作者：
MOYER, MP;SHIURBA, JF;RAPOPORT, H
通过Batcho-Leimgruber方法方便地合成的4-、5-、6-和7-溴吲哚用作区域化学纯的锂化吲哚的有效前体。如果首先使用氢化钾来去除酸性吲哚NH，然后使用叔丁基锂来实现金属-卤素交换，则金属-卤素交换是最有效的。所得到的吲哚基有机金属试剂与各种亲电试剂反应，得到区域异构纯的酰化吲哚。
The 4-,5-,6-, and 7-bromoindoles, conveniently synthesized by the Batcho-Leimgruber process, serve as efficient precursors to regiochemically pure lithiated indoles. Metal-halogen exchange was most effective if potassium hydride was used first to remove the acidic indole NH, and tert-butyllithium was used then to effect metal-halogen exchange. The resulting indolyl organometallic reagents react with a variety of electrophiles to give regioisomerically pure acylated indoles.