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Decarbonylative Olefination of Aldehydes to Alkenes

preprint
submitted on 25.10.2019 and posted on 28.10.2019 by Diana Ainembabazi, Christopher Reid, Amanda Chen, Jakub Kostal, Adelina Voutchkova-Kostal
New atom-economical alternatives to Wittig chemistry are needed construct olefins from carbonyl complexes, but none have been developed to-date. Here we report an atom-economical olefination of carbonyls via aldol-decarbonylative coupling of aldehydes using robust and recyclable supported Pd catalysts, producing only CO and H2O as waste. The reaction accommodates homocoupling of aldehydes with an a a-methylene groups, as well as heterocoupling. Computations provide insight into the selectivity of the reaction. The tandem aldol-decarbonylation reaction opens the door to exploration of new carbonyl reactivity to construct olefins.

Funding

NSF CBET

History

Email Address of Submitting Author

avoutchkova@gwu.edu

Institution

George Washington Universty

Country

USA

ORCID For Submitting Author

0000-0002-7016-5244

Declaration of Conflict of Interest

No conflict

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in Journal of the American Chemical Society

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