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3. Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C–H borylation–cross-coupling sequence

Author

Norio Miyaura, Yusuke Nobuta, Takao Kikuchi, Junko Umeda, Tatsuo Ishiyama, and Yasunori Yamamoto

Subjects
Pinacol, Organic Chemistry, One-pot synthesis, Sequence (biology), Biochemistry, Borylation, Medicinal chemistry, Catalysis, Hexane, chemistry.chemical_compound, biaryls, chemistry, pinacolborane, Drug Discovery, cross-coupling, Organic chemistry, boron, C-H activation
Abstract

A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C–H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) at 25 °C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 °C in the presence of PdCl2(dppf) (3.0 mol %) and K3PO4 in DMF. This one-pot, two-step procedure provided a variety of unsymmetrical biaryls in high yields.

Published
2008

4. ChemInform Abstract: Practical Synthesis of Pinacolborane for One-Pot Synthesis of Unsymmetrical Biaryls via Aromatic C-H Borylation-Cross-Coupling Sequence

Author

Junko Umeda, Yasunori Yamamoto, Norio Miyaura, Tatsuo Ishiyama, Yusuke Nobuta, and Takao Kikuchi

Subjects
Hexane, chemistry.chemical_compound, chemistry, Pinacol, One-pot synthesis, Sequence (biology), General Medicine, Medicinal chemistry, Borylation, Catalysis
Abstract

A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C–H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) at 25 °C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 °C in the presence of PdCl2(dppf) (3.0 mol %) and K3PO4 in DMF. This one-pot, two-step procedure provided a variety of unsymmetrical biaryls in high yields.

Published
2008
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5. Iridium-Catalyzed C-H Borylation of Arenes and Heteroarenes: 1-Chloro-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene and 2-(4,4,5,5,-Tetramethyl-1,3,2-dioxaborolan-2-yl)indole

Author

Norio Miyaura, Jun Takagi, Tatsuo Ishiyama, and Yusuke Nobuta

Subjects
Indole test, chemistry.chemical_compound, chemistry, Aryl, chemistry.chemical_element, Organic chemistry, Regioselectivity, Iridium, Benzene, Borylation, Medicinal chemistry, Catalysis, Waste disposal
Abstract

Bis(η4-1,5-cyclooctadiene)-di μ-methoxy-diiridium(1) 4,4′-Di-tert-butyl-2,2′-bipyridine Bis(pinacolato)diboron 1-Chloro-3-iodobenzene Pinacolborane Indole Keywords: iridium catalysts; borylation; arenes; heteroarenes; aryl boron derivatives; heteroarylboron derivatives; boronates; regiochemistry; waste disposal; magnesium; lithium

Published
2005
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6. Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent

Author

Yusuke Nobuta, Norio Miyaura, John F. Hartwig, and Tatsuo Ishiyama

Subjects
Inert, Aryl, chemistry.chemical_element, General Medicine, Borylation, Catalysis, Hexane, Solvent, chemistry.chemical_compound, chemistry, Polymer chemistry, Iridium, Stoichiometry
Abstract

Aromatic C-H borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane was catalyzed by an iridium complex generated from 1/2[Ir(OMe)(COD)]2 and 4,4'-di-tert-butyl-2,2'-bipyridine at room temperature in hexane and afforded the corresponding aryl- and heteroarylboronates in high yields with excellent regioselectivities.

Published
2003

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