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 BA 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.
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