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JACS_comm_ChemRx.pdf (369.83 kB)
Decarbonylative Olefination of Aldehydes to Alkenes
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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.