Work

Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles

Year: 2012

Type: article

Abstract: The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4,5-dihydro-2-oxazolyl)quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated S(N)2-type stereoinvertive oxidative addition of unactivated primary and secondary alkyl tosylates.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja305403s

Authors: Benjamin J. Stokes, Susanne M. Opra, Matthew S. Sigman

Institution: University of Utah

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Pd(0)-Catalyzed Allylic C-H Functionalization Reactions of Homoallylic Tosylates, Pd-Catalyzed Olefin Functionalization Reactions for Organic Synthesis