Iridium-catalyzed borylation of arenes and heteroarenes via C–H activation*
نویسندگان
چکیده
Direct C–H borylation of aromatic compounds catalyzed by a transition-metal complex was studied as an economical protocol for the synthesis of aromatic boron derivatives. Iridium complexes generated from Ir(I) precursors and 2,2'-bipyridine ligands efficiently catalyzed the reactions of arenes and heteroarenes with bis(pinacolato)diboron or pinacolborane to produce a variety of aryland heteroarylboron compounds. The catalytic cycle involves the formation of a tris(boryl)iridium(III) species and its oxidative addition to an aromatic C–H bond.
منابع مشابه
Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane
Catalytic C-H borylation of arenes has been widely used in organic synthesis because it allows the introduction of a versatile boron functionality directly onto simple, unfunctionalized arenes. We report herein the use of diisopropylaminoborane as a boron source in C-H borylation of arenes. An iridium(I) complex with 1,3-dicyclohexylimidazol-2-ylidene is found to efficiently catalyze the boryla...
متن کاملIridium-bipyridine periodic mesoporous organosilica catalyzed direct C-H borylation using a pinacolborane.
Heterogeneous catalysis for direct C-H borylation of arenes and heteroarenes in the combination of iridium (Ir) complex fixed on periodic mesoporous organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinaco...
متن کاملCREATED USING THE RSC CHEMCOMM TEMPLATE - SEE WWW.RSC.ORG/ELECTRONICFILES FOR DETAILS Room temperature borylation of arenes and heteroarenes by stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent†
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Multidirectional Synthesis of Substituted Indazoles via Iridium-Catalyzed C-H Borylation.
In the absence of a steric directing group, iridium-catalyzed C-H borylation of N-protected indazoles occurs rapidly and selectively at C-3 and the resulting boronate esters can be utilized in a range of downstream conversions. The functional group tolerance of the iridium-catalyzed C-H borylation reaction enables simple and efficient multidirectional syntheses of substituted indazoles to be re...
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Unsaturated σ,π-cyclooctenyl and hydrido Ir(III) complexes bearing an unusual tridentate dianionic ONO pincer-type ligand have been straightforwardly obtained from 2,6-pyridinedicarboxylic acid and standard Ir(I) starting materials. These complexes efficiently catalyzed the arene C-H borylation under thermal conditions.
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