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Facile Pyridine S _N Ar Reactions via N-Phosphonium-Pyridinium Intermediates.

ABSTRACT: Here we report that N-phosphonium pyridinium intermediates are unusually reactive for pyridine S _N Ar reactions. Specifically, forming phosphonium salts from halopyridines typically requires elevated temperatures and Lewis acid additives. The alternative activation mode described in this paper permits C-P bond formation to occur at ambient temperatures in many cases, and functions across a broad range of substrates.

SUBMITTER: Boyle BT

PROVIDER: S-EPMC8081384 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Facile Pyridine S N Ar Reactions via N-Phosphonium-Pyridinium Intermediates.

Boyle Benjamin T BT Koniarczyk J Luke JL McNally Andrew A

Synlett : accounts and rapid communications in synthetic organic chemistry 20201119 2

Here we report that N-phosphonium pyridinium intermediates are unusually reactive for pyridine S N Ar reactions. Specifically, forming phosphonium salts from halopyridines typically requires elevated temperatures and Lewis acid additives. The alternative activation mode described in this paper permits C-P bond formation to occur at ambient temperatures in many cases, and functions across a broad range of substrates. ...[more]

PMID: 33927483

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