Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one

Jivan Shinde, Veerababurao Kavala, Ching Fa Yao*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

This Letter outlines palladium-catalyzed regioselective (Markovnikov’s) addition of aryl boronic acids to propargyl 1,3-dicarbonyl alkyne to accomplish olefinic/diene 1,3-dicarbonyl compounds without the need for water workup. This methodology showcases remarkable performance with wide-ranging substrate diversity, achieving high yields while employing merely 3 mol % [Pd] alongside a mild KOAc base. Moreover, the utility of dicarbonyl olefins is exemplified through their application in intramolecular cyclization and debenzoylation reactions to access valuable trisubstituted pyran building blocks and (E)-4-methylene-1,6-diphenylhex-5-en-1-one synthesis.

Original languageEnglish
Pages (from-to)6943-6948
Number of pages6
JournalOrganic Letters
Volume25
Issue number38
DOIs
Publication statusPublished - 2023 Sept 29

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Pd-Catalyzed Regioselective (Markovnikov) Addition of Aryl Boronic Acids to Terminal Alkynes of 1,3-Dicarbonyl Compounds and Cyclization/Debenzoylation of Olefinic Dicarbonyl: Access to Arylated Pyran and (E)-4-Methylene-1,6-diphenylhex-5-en-1-one'. Together they form a unique fingerprint.

Cite this