Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C-H bond activation

Takeshi Yamakawa, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

An ortho-alkenylation reaction of an aromatic aldimine with an internal alkyne is efficiently promoted by a cobalt catalyst generated from CoBr 2, triarylphosphine, and iPrMgBr. The reaction takes place under mild room-temperature conditions to afford, upon acidic hydrolysis, a variety of ortho-alkenylated aromatic aldehydes in moderate to excellent yields. The neighboring formyl and alkenyl groups in the product can be utilized as synthetic handles for the facile construction of indene and naphthalene carbocycles.

Original languageEnglish
Pages (from-to)4459-4465
Number of pages7
JournalTetrahedron
Volume69
Issue number22
DOIs
Publication statusPublished - 2013 Jun 3
Externally publishedYes

Keywords

  • Aldimine
  • Alkyne
  • C-H bond functionalization
  • Carbocycles
  • Cobalt catalysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Cobalt-catalyzed ortho-alkenylation of aromatic aldimines via chelation-assisted C-H bond activation'. Together they form a unique fingerprint.

Cite this