Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters

Ryoichi Kuwano, Yutaka Kondo, Yosuke Matsuyama

Research output: Contribution to journalArticle

124 Citations (Scopus)

Abstract

A palladium complex generated in situ from [Pd(η3-C3H5)(cod)]BF4 and DPPF is a good catalyst for benzylic alkylation of benzyl methyl carbonate with the carbanion of dimethyl malonates. The catalytic reaction is applicable to a wide range of the benzylations of benzylic esters with malonates. The catalytic activity was heavily affected by the bite angle of the bidentate phosphine ligand on palladium. DPEphos ligand is superior to DPPF in the case of palladium-catalyzed benzylic amination of benzylic esters.

Original languageEnglish
Pages (from-to)12104-12105
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number40
DOIs
Publication statusPublished - Oct 8 2003

Fingerprint

Palladium
Esters
phosphine
Substitution reactions
Malonates
Ligands
Amination
Gadiformes
Alkylation
Bites and Stings
Carbonates
Catalyst activity
Catalysts

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters. / Kuwano, Ryoichi; Kondo, Yutaka; Matsuyama, Yosuke.

In: Journal of the American Chemical Society, Vol. 125, No. 40, 08.10.2003, p. 12104-12105.

Research output: Contribution to journalArticle

Kuwano, Ryoichi ; Kondo, Yutaka ; Matsuyama, Yosuke. / Palladium-catalyzed nucleophilic benzylic substitutions of benzylic esters. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 40. pp. 12104-12105.
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