Oxidative Dearomatization of Pyridines

Zohaib Siddiqi, Tanner W. Bingham, Tsukasa Shimakawa, Kevin D. Hesp, Andre Shavnya, David Sarlah

Research output: Contribution to journalArticlepeer-review

Abstract

Dearomatization of pyridines is a well-established synthetic approach to access piperidines. Although remarkably powerful, existing dearomatization processes have been limited to the hydrogenation or addition of carbon-based nucleophiles to activated pyridiniums. Here, we show that arenophile-mediated dearomatizations can be applied to pyridines to directly introduce heteroatom functionalities without prior substrate activation. The arenophile platform in combination with olefin oxidation chemistry provides access to dihydropyridine cis-diols and epoxides. These previously elusive compounds are now readily accessible and can be used for the downstream preparation of diversely functionalized piperidines.

Original languageEnglish (US)
Pages (from-to)2358-2363
Number of pages6
JournalJournal of the American Chemical Society
Volume146
Issue number4
DOIs
StatePublished - Jan 31 2024

ASJC Scopus subject areas

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry

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