Site-selective C-H borylation of quinolines at the C8 position catalyzed by a silica-supported phosphane-iridium system.

  title={Site-selective C-H borylation of quinolines at the C8 position catalyzed by a silica-supported phosphane-iridium system.},
  author={Shota Konishi and Soichiro Kawamorita and Tomohiro Iwai and Patrick G. Steel and Todd B. Marder and Masaya Sawamura},
  journal={Chemistry, an Asian journal},
  volume={9 2},
Site-selective C-H borylation of quinoline derivatives at the C8 position has been achieved by using a heterogeneous Ir catalyst system based on a silica-supported cage-type monophosphane ligand SMAP. The efficient synthesis of a corticotropin-releasing factor1 (CRF1) receptor antagonist based on a late-stage C-H borylation strategy demonstrates the utility of the C8 borylation reaction. 
82 Citations

Multidirectional Synthesis of Substituted Indazoles via Iridium-Catalyzed C-H Borylation.

The functional group tolerance of the iridium-catalyzed C-H borylation reaction enables simple and efficient multidirectional syntheses of substituted indazoles to be realized.

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C8-Selective Acylation of Quinoline N-Oxides with α-Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C-H Bond Activation.

A facile and efficient protocol for palladium-catalyzed C8-selective acylation of quinoline N-oxides with α-oxocarboxylic acids has been developed under mild reaction conditions with excellent regioselectivity and broad functional group tolerance.

Zinc-Catalyzed Dual C-X and C-H Borylation of Aryl Halides.

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Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters.

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Enantioselective Rh- or Ir-catalyzed Directed C(sp3)–H Borylation with Phosphoramidite Chiral Ligands

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Ru-Catalyzed Deoxygenative Regioselective C8-H Arylation of Quinoline N-Oxides.

Mechanistic studies revealed that the development of Ru-catalyzed deoxygenative regioselective C8 arylation of quinoline N-oxides with arylboronic esters proceeds in a tandem process of aRYlation and then de oxygengenation, wherein both steps were found to be catalytic with the ruthenium species.



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Rh(NHC)-catalyzed direct and selective arylation of quinolines at the 8-position.

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Directed ortho borylation of phenol derivatives catalyzed by a silica-supported iridium complex.

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The first direct borylation of a C-H bond at the 4-position of pyrene was achieved using [Ir(COD)Cl](2)/dtbpy as the catalyst precursor and B(2)pin(2) as the boron source. The position-related

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The site-selective activation and borylation of unactivated C(sp(3))-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir

Iridium-catalyzed C-H activation versus directed ortho metalation: complementary borylation of aromatics and heteroaromatics.

A new concept, the use of the TMS group, readily introduced by DoM, as a latent regiodirective moiety to overcome the otherwise problematic production of isomeric borylated product mixtures is presented.

Directed ortho borylation of functionalized arenes catalyzed by a silica-supported compact phosphine-iridium system.

An immobilized monophosphine-Ir system, which was prepared in situ from [Ir(OMe)(cod)](2) and a silica-supported, compact phosphine, showed high activities and selectivities for the borylation of

Formation of Aryl- and Benzylboronate Esters by Rhodium-Catalyzed C-H Bond Functionalization with Pinacolborane.

Direct borylation of C-H bonds in aromatic compounds can be achieved by using the efficient homogeneous catalyst precursor [RhCl(PiPr3 )2 (N2 )] and pinacolborane (HBpin; see scheme). High