Palladium-catalyzed Nucleophilic Substitution of Benzylic Esters

DOI Web Site 112 References
  • Kuwano Ryoichi
    Department of Chemistry, Graduate School of Sciences, Kyushu University

Bibliographic Information

Other Title
  • パラジウム触媒によるベンジルエステル類の求核置換反応
  • パラジウム ショクバイ ニ ヨル ベンジルエステルルイ ノ キュウカク チカン ハンノウ

Search this article

Abstract

We found that benzylic carbonates or acetates undergo nucleophilic substitution in the presence of a palladium complex. The palladium catalyst, which is prepared in situ from [Pd(η3-C3H5)(cod)]BF4 and bidentate bisphosphine DPPF, is effective for the reaction of benzyl carbonate with malonate carbanion, giving the desired benzylmalonate in high yield. Choice of the ligand is crucial for the palladium catalysis. Amines, phenols, and sulfinates work as nucleophiles for the palladium-catalyzed benzylic substitution. The activation of the benzylic carbon-oxygen bond with the palladium complex is applied to the cross-coupling of benzyl esters with organometallic compounds or the [4+2] cycloaddition of o-(silylmethyl)benzyl carbonates with alkenes. The latter reaction is equivalent to the Diels-Alder reaction of ortho-quinodimethanes with dienophiles.

Journal

References(112)*help

See more

Related Projects

See more

Keywords

Details 詳細情報について

Report a problem

Back to top