Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Trifluoromethanesulfonate-Catalyzed Allylation of Dioxolanes

Matthew J. Spafford; James E. Christensen; Matthew G. Huddle; Joshua R. Lacey; Ram S. Mohan; Matthew J. Spafford; James E. Christensen; Matthew G. Huddle; Joshua R. Lacey; Ram S. Mohan

doi:10.1071/CH08109

RESEARCH ARTICLE

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Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Trifluoromethanesulfonate-Catalyzed Allylation of Dioxolanes

Matthew J. Spafford ^A , James E. Christensen ^A , Matthew G. Huddle ^A , Joshua R. Lacey ^A and Ram S. Mohan ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61701, USA.

^B Corresponding author. Email: rmohan@iwu.edu

Australian Journal of Chemistry 61(6) 419-421 https://doi.org/10.1071/CH08109
Submitted: 17 March 2008 Accepted: 28 April 2008 Published: 19 June 2008

Abstract

A bismuth trifluoromethanesulfonate (triflate)-catalyzed (2.0 mol-%) multicomponent reaction involving the allylation of dioxolanes followed by in situ derivatization with anhydrides to generate highly functionalized esters has been developed under solvent-free conditions. Most reagents used to date for allylation of dioxolanes are highly corrosive and are often required in stoichiometric amounts. In contrast, the use of a relatively non-toxic and non-corrosive bismuth(iii)-based catalyst makes this methodology especially attractive for scale-up.

Acknowledgements

The authors gratefully acknowledge funding from the National Science Foundation for an RUI (Research at Undergraduate Institutions) grant (no. 0650682) awarded to R.S.M.

References

Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Trifluoromethanesulfonate-Catalyzed Allylation of Dioxolanes

Abstract

Acknowledgements

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