Abstract

The reaction of perfluoropyridines with indoles and bis(indolyl)methanes (BIMs) was investigated. The aromatic nucleophilic substitution of pentafluoropyridine with indoles occurs at the 4-position of pyridine ring by nitrogen site of indolyl anion, while reaction with 2,3,5,6-tetrafluoro-4-(phenylsulfonyl)pyridine gave a mixture of products arising substitution at 2-position of pyridine ring and replacement of phenylsulfonyl group. Furthermore, the reaction of pentafluoropyridine with BIMs yielded mixture of mono- and bis-perfluoropyridyl products.

Graphic abstract

中文翻译：

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通过全氟吡啶与吲哚化合物的反应使吲哚全氟吡啶化

摘要

研究了全氟吡啶与吲哚和双（吲哚基）甲烷（BIM）的反应。五氟吡啶被吲哚的芳族亲核取代发生在吡啶环的4位上，吲哚阴离子的氮原子位置，而与2,3,5,6-四氟-4-（苯磺酰基）吡啶的反应则产生了取代产物在吡啶环的2-位上取代苯基磺酰基。此外，五氟吡啶与BIM的反应产生了单-和双-全氟吡啶基产物的混合物。

图形摘要