Heteroaromatic benzyl ethers as intermediates for palladium-catalysed transfer hydrogenolysis of benzyl alcohols

Araujo, Nuna C. P.; Brigas, Amadeu; Cristiano, Maria Lurdes Santos; Frija, L.; Guimarães, Emanuel M. O.; Loureiro, Rui M. S.

http://hdl.handle.net/10400.1/4259

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Authors

Araujo, Nuna C. P.

Brigas, Amadeu

Cristiano, Maria Lurdes Santos

Frija, L.

Guimarães, Emanuel M. O.

Loureiro, Rui M. S.

Abstract(s)

A chemoselective and easy to carry procedure for the hydrogenolysis of benzyl alcohols is described. Benzyl alcohols are readily converted into tetrazolyl and benzisothiazolyl ethers that can be catalytically hydrogenolysed to toluenes over palladium-on-charcoal using hydrogen donors. The effect of electronwithdrawing heteroaromatic substituents is interpreted on the basis of chrystallographic structure determinations and molecular orbital calculations.

Keywords

Palladium-on-charcoal Transfer hydrogenolysis Tetrazoles Benzisothiazoles

URI

http://hdl.handle.net/10400.1/4259

Citation

Araújo, Nuna C.P; Brigas, Amadeu F; Cristiano, M.Lurdes S; Frija, Lui¿?s M.T; Guimarães, Emanuel M.O; Loureiro, Rui M.S. Heteroaromatic benzyl ethers as intermediates for palladium-catalysed transfer hydrogenolysis of benzyl alcohols, Journal of Molecular Catalysis A: Chemical, 215, 1-2, 113-120, 2004.