Literature DB >> 25966913

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

David E Stephens1, Johant Lakey-Beitia, Gabriel Chavez, Carla Ilie, Hadi D Arman, Oleg V Larionov.   

Abstract

A novel site-selective palladium-catalyzed oxidative C8-H homocoupling reaction of quinoline N-oxides has been developed. The reaction affords substituted 8,8'-biquinolyl N,N'-dioxides that can be readily converted to a variety of functionalized 8,8'-biquinolyls. Mechanistic studies point to the crucial role of the oxidant and a non-innocent behavior of acetic acid as a solvent.

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Year:  2015        PMID： 25966913      PMCID： PMC4714569          DOI： 10.1039/c5cc02227d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  31 in total

1.  Three-component coupling of arynes and organic bromides.

Authors:  Hiroto Yoshida; Yuji Asatsu; Yasuhiro Mimura; Yu Ito; Joji Ohshita; Ken Takaki
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-02       Impact factor: 15.336

2.  Palladium-catalyzed C-H homocoupling of bromothiophene derivatives and synthetic application to well-defined oligothiophenes.

Authors:  Masabumi Takahashi; Kentaro Masui; Hiroki Sekiguchi; Nobuhiko Kobayashi; Atsunori Mori; Masahiro Funahashi; Nobuyuki Tamaoki
Journal:  J Am Chem Soc       Date:  2006-08-23       Impact factor: 15.419

3.  Highly regioselective catalytic oxidative coupling reactions: synthetic and mechanistic investigations.

Authors:  Kami L Hull; Erica L Lanni; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2006-11-01       Impact factor: 15.419

4.  Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.

Authors:  Oleg V Larionov; David Stephens; Adelphe Mfuh; Gabriel Chavez
Journal:  Org Lett       Date:  2014-01-10       Impact factor: 6.005

5.  Nickel, manganese, cobalt, and iron-catalyzed deprotonative arene dimerization.

Authors:  Thanh Truong; Joseph Alvarado; Ly Dieu Tran; Olafs Daugulis
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

6.  Palladium-catalyzed regioselective oxidative coupling of indoles and one-pot synthesis of acetoxylated biindolyls.

Authors:  Zunjun Liang; Jinlong Zhao; Yuhong Zhang
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

Review 7.  Structure and function of "metalloantibiotics".

Authors:  Li-June Ming
Journal:  Med Res Rev       Date:  2003-11       Impact factor: 12.944

8.  Pd-catalyzed decarboxylative cross-coupling of 2-carboxyazine N-oxides with various (hetero)aryl halides.

Authors:  Jean-Baptiste Rouchet; Cédric Schneider; Cédric Spitz; Johan Lefèvre; George Dupas; Corinne Fruit; Christophe Hoarau
Journal:  Chemistry       Date:  2014-02-26       Impact factor: 5.236

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

Authors:  Shota Konishi; Soichiro Kawamorita; Tomohiro Iwai; Patrick G Steel; Todd B Marder; Masaya Sawamura
Journal:  Chem Asian J       Date:  2014-02

10.  Insights into the mechanistic and synthetic aspects of the Mo/P-catalyzed oxidation of N-heterocycles.

Authors:  Oleg V Larionov; David Stephens; Adelphe M Mfuh; Hadi D Arman; Anastasia S Naumova; Gabriel Chavez; Behije Skenderi
Journal:  Org Biomol Chem       Date:  2014-05-21       Impact factor: 3.876
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  7 in total

1.  Organocatalytic Synthesis of Methylene-Bridged N-Heterobiaryls.

Authors:  David E Stephens; Vu T Nguyen; Bhuwan Chhetri; Emily R Clark; Hadi D Arman; Oleg V Larionov
Journal:  Org Lett       Date:  2016-11-03       Impact factor: 6.005

Review 2.  Heterocyclic N-Oxides - An Emerging Class of Therapeutic Agents.

Authors:  A M Mfuh; O V Larionov
Journal:  Curr Med Chem       Date:  2015       Impact factor: 4.530

3.  Mechanistic insights into the potassium tert-butoxide-mediated synthesis of N-heterobiaryls.

Authors:  David E Stephens; Johant Lakey-Beitia; Jessica E Burch; Hadi D Arman; Oleg V Larionov
Journal:  Chem Commun (Camb)       Date:  2016-08-02       Impact factor: 6.222

4.  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

5.  Highly Stereoselective and Catalytic Desulfitative C-O and C-I Dienylation with Sulfolenes: the Importance of Basic Additives.

Authors:  Hang T Dang; Viet D Nguyen; Hoang H Pham; Hadi D Arman; Oleg V Larionov
Journal:  Tetrahedron       Date:  2019-04-08       Impact factor: 2.457

Review 6.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

7.  Relative Strength of Common Directing Groups in Palladium-Catalyzed Aromatic C-H Activation.

Authors:  Anna Tomberg; Michael Éric Muratore; Magnus Jan Johansson; Ina Terstiege; Christian Sköld; Per-Ola Norrby
Journal:  iScience       Date:  2019-09-27
  7 in total

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