Accessing Illusive e Isomers of α-Ester Hydrazones via Visible-Light-Induced Pd-Catalyzed Heck-Type Alkylation

Nikita Kvasovs, Vladimir Gevorgyan

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A visible-light-induced Pd-catalyzed stereoselective synthesis of alkylated ester hydrazones has been developed. This method operates via generation of a nucleophilic carbon-centered radical from alkyl bromide, iodide, or redox-Active ester, followed by its addition to hydrazone, and a subsequent desaturation by palladium. The majority of products have E configuration, which are inaccessible by conventional condensation methods. In addition, a sequential C,N-Alkylation protocol has been developed: A reaction between 1,3-dihalides and glyoxylate-derived hydrazone, delivering tetrahydropyridazines.

Original languageEnglish (US)
Pages (from-to)4176-4181
Number of pages6
JournalOrganic Letters
Volume24
Issue number23
DOIs
StatePublished - Jun 17 2022
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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