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Mechanistic Study and Development of Catalytic Reactions of Sm(II)

preprint
submitted on 16.11.2018 and posted on 19.11.2018 by Sandepan Maity, Robert Flowers
Despite the broad utility and application of SmI2in synthesis, the reagent is used in stoichiometric amounts and has a high molecular weight, resulting in a large amount of material being used for reactions requiring one or more equivalents of electrons. We report mechanistic studies on catalytic reactions of Sm(II) employing a terminal magnesium reductant and trimethyl silyl chloride in concert with a non-coordinating proton donor source. Reactions using this approach permitted reductions with as little as 1 mol% Sm. The mechanistic approach enabled catalysis employing HMPA as a ligand, facilitating the development of catalytic Sm(II) 5-exo-trig ketyl olefin cyclization reactions.

Funding

NSF CHE 1565741

History

Email Address of Submitting Author

rof2@lehigh.edu

Institution

Lehigh University, Department of Chemistry

Country

USA

ORCID For Submitting Author

0000-0003-2295-1336

Declaration of Conflict of Interest

No conflict of interest

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in Journal of the American Chemical Society

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