Angewandte Chemie International Edition · 2019 · 43 citations · 67 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryAlkyne ComplexesReaction MechanismsAlkane FunctionalizationAlkyne Iridium ComplexesBorylation ReactionsHydroboration Of AlkynesOrganoiridium ChemistryRegioselectivityTransition-metal-catalyzed Functionalization
Abstract The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium‐catalyzed hydroboration of aliphatic internal alkenes, providing distal‐borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C−B bond of the distal‐borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected Ir III /Ir V cycle.
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Enantiospecific sp2–sp3 coupling of secondary and tertiary boronic esters
Amadeu Bonet, Marcin Odachowski, Daniele Leonori et al. · Nature Chemistry · 2014 · 429 citations · Full text