Literature DB >> 25202762

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

Shota Konishi, Soichiro Kawamorita, Tomohiro Iwai, Patrick G Steel, Todd B Marder, Masaya Sawamura.   

Abstract

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.

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Year:  2014        PMID： 25202762     DOI： 10.1002/asia.201301423

Source DB:  PubMed          Journal:  Chem Asian J        ISSN： 1861-471X


  9 in total

1.  Experimental and mechanistic analysis of the palladium-catalyzed oxidative C8-selective C-H homocoupling of quinoline N-oxides.

Authors:  David E Stephens; Johant Lakey-Beitia; Gabriel Chavez; Carla Ilie; Hadi D Arman; Oleg V Larionov
Journal:  Chem Commun (Camb)       Date:  2015-06-11       Impact factor: 6.222

2.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457

3.  Palladium-Catalyzed C8-Selective C-H Arylation of Quinoline N-Oxides: Insights into the Electronic, Steric and Solvation Effects on the Site-Selectivity by Mechanistic and DFT Computational Studies.

Authors:  David E Stephens; Johant Lakey-Beitia; Abdurrahman C Atesin; Tülay A Ateşin; Gabriel Chavez; Hadi D Arman; Oleg V Larionov
Journal:  ACS Catal       Date:  2015-01-02       Impact factor: 13.084

4.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

5.  Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C-H Activation.

Authors:  Geraint H M Davies; Matthieu Jouffroy; Fatemeh Sherafat; Borna Saeednia; Casey Howshall; Gary A Molander
Journal:  J Org Chem       Date:  2017-07-17       Impact factor: 4.354

6.  Mechanism, reactivity, and selectivity of the iridium-catalyzed C(sp3)-H borylation of chlorosilanes.

Authors:  Genping Huang; Marcin Kalek; Rong-Zhen Liao; Fahmi Himo
Journal:  Chem Sci       Date:  2014-12-04       Impact factor: 9.825

7.  Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions.

Authors:  Xinxin Qi; Li-Bing Jiang; Chao Zhou; Jin-Bao Peng; Xiao-Feng Wu
Journal:  ChemistryOpen       Date:  2017-03-16       Impact factor: 2.911

8.  Iridium-Catalyzed Borylation of 6-Fluoroquinolines: Access to 6-Fluoroquinolones.

Authors:  Aobha Hickey; Julia Merz; Hamad H Al Mamari; Alexandra Friedrich; Todd B Marder; Gerard P McGlacken
Journal:  J Org Chem       Date:  2022-07-15       Impact factor: 4.198

9.  Electronically Driven Regioselective Iridium-Catalyzed C-H Borylation of Donor-π-Acceptor Chromophores Containing Triarylboron Acceptors.

Authors:  Florian Rauch; Johannes Krebs; Julian Günther; Alexandra Friedrich; Martin Hähnel; Ivo Krummenacher; Holger Braunschweig; Maik Finze; Todd B Marder
Journal:  Chemistry       Date:  2020-07-23       Impact factor: 5.236
  9 in total

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