Organic Letters · 2018 · 92 citations · 67 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst PreparationCatalytic MaterialsOrganic SynthesisAlkane FunctionalizationC - H Bond FunctionalizationChemoselective FunctionalizationChemoselective SynthesisCobalt CatalysisHydroboration Of AlkynesKetone FunctionalizationMild Reaction Conditions
An operationally convenient and general method for hydroboration of alkenes, aldehydes, and ketones employing Co(acac)3 as a precatalyst is reported. The hydroboration of alkenes in the presence of HBpin, PPh3, and NaOtBu affords good to excellent yields with high Markovnikov selectivity with up to 97:3 branched/linear selectivity. Moreover, Co(acac)3 could be used effectively to hydroborate aldehydes and ketones in the absence of additives under mild reaction conditions. Inter- and intramolecular chemoselective reduction of the aldehyde group took place over the ketone functional group.
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Hydroborations catalysed by transition metal complexes
I. P. Beletskaya, Andrew Pelter · Tetrahedron · 1997 · 618 citations