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A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides.

ABSTRACT: Indoles are among the most important N-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl diazoniums that sequentially activate the alkyl iodides through halogen-atom transfer and then serve as radical acceptors. The process operates under mild conditions and enables the preparation of densely functionalized indoles.

SUBMITTER: Govaerts S

PROVIDER: S-EPMC9641658 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides.

Govaerts Sebastian S Nakamura Kento K Constantin Timothée T Leonori Daniele D

Organic letters 20221021 43

Indoles are among the most important <i>N</i>-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated strategy features a double role for the aryl diazoniums that sequentially activate the alkyl iodides through halogen-atom transfer and then serve as radical acceptors. The process operates under mild conditions and enables the preparation of densely functio ...[more]

PMID: 36268790

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