Literature DB >> 27397938

Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Tian-Sheng Mei1, Lei Kou1, Sandy Ma1, Keary M Engle1, Jin-Quan Yu1.   

Abstract

Heterocyclic compounds are ubiquitous in natural products, pharmaceuticals, and agrochemicals. Therefore, the design of novel protocols to construct heterocycles more efficiently is a major area of focus in the organic chemistry. In the past several years, cyclization reactions based upon pan class="Chemical">palladium-catalyzed C-H activation have received substantial attention due to their caclass="Chemical">pacity for expediting heterocycle synthesis. This review discusses strategies for heterocycle synthesis via class="Chemical">pan class="Chemical">palladium-catalyzed C-H bond activation and highlights recent examples from the literature.

Entities:  

Keywords:  C–H activation; Heterocycle; amination; carbonylation; olefination

Year:  2012        PMID: 27397938      PMCID: PMC4936280          DOI: 10.1055/s-0031-1289766

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  129 in total

1.  Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

Authors:  Jwanro Hassan; Marc Sévignon; Christel Gozzi; Emmanuelle Schulz; Marc Lemaire
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: reactions and mechanistic aspects.

Authors:  Vincent Ritleng; Claude Sirlin; Michel Pfeffer
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

3.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

Review 4.  Sigma-chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover.

Authors:  Jin-Quan Yu; Ramesh Giri; Xiao Chen
Journal:  Org Biomol Chem       Date:  2006-11-21       Impact factor: 3.876

5.  Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

Authors:  Sean A Reed; M Christina White
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

6.  C-H functionalization logic in total synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  Chem Soc Rev       Date:  2011-02-07       Impact factor: 54.564

7.  Synthesis of 3-(diarylmethylenyl)oxindole by a palladium-catalyzed domino carbopalladation/C-H activation/C-C bond-forming process.

Authors:  Artur Pinto; Luc Neuville; Pascal Retailleau; Jieping Zhu
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

8.  Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: expedient routes to anthranilic acids, oxazolinones, and quinazolinones.

Authors:  Ramesh Giri; Jonathan K Lam; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

Review 9.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384

10.  Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling.

Authors:  David R Stuart; Elisia Villemure; Keith Fagnou
Journal:  J Am Chem Soc       Date:  2007-09-19       Impact factor: 15.419

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  10 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

Authors:  Kyle Clagg; Haiyun Hou; Adam B Weinstein; David Russell; Shannon S Stahl; Stefan G Koenig
Journal:  Org Lett       Date:  2016-07-12       Impact factor: 6.005

3.  Ruthenium-Catalyzed C-H Bond Activation Approach to Azolyl Aminals and Hemiaminal Ethers, Mechanistic Evaluations, and Isomer Interconversion.

Authors:  Manish K Singh; Hari K Akula; Sakilam Satishkumar; Lothar Stahl; Mahesh K Lakshman
Journal:  ACS Catal       Date:  2016-02-18       Impact factor: 13.084

Review 4.  Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors:  Keary M Engle; Jin-Quan Yu
Journal:  J Org Chem       Date:  2013-05-03       Impact factor: 4.354

Review 5.  Recent advances in the electrochemical construction of heterocycles.

Authors:  Robert Francke
Journal:  Beilstein J Org Chem       Date:  2014-12-03       Impact factor: 2.883

6.  Merging rhodium-catalysed C-H activation and hydroamination in a highly selective [4+2] imine/alkyne annulation.

Authors:  Rajith S Manan; Pinjing Zhao
Journal:  Nat Commun       Date:  2016-06-20       Impact factor: 14.919

7.  Palladium-catalyzed picolinamide-directed iodination of remote ortho-C-H bonds of arenes: Synthesis of tetrahydroquinolines.

Authors:  William A Nack; Xinmou Wang; Bo Wang; Gang He; Gong Chen
Journal:  Beilstein J Org Chem       Date:  2016-06-17       Impact factor: 2.883

8.  A novel Pd-catalysed sequential carbonylation/cyclization approach toward bis-N-heterocycles: rationalization by electronic structure calculations.

Authors:  Liliana Damas; Rui M B Carrilho; Sandra C C Nunes; Alberto A C C Pais; László Kollár; Marta Pineiro; Mariette M Pereira
Journal:  R Soc Open Sci       Date:  2018-09-12       Impact factor: 2.963

9.  Remote Construction of N-Heterocycles via 1,4-Palladium Shift-Mediated Double C-H Activation.

Authors:  Takeru Miyakoshi; Nadja E Niggli; Olivier Baudoin
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-23       Impact factor: 16.823

10.  A bio-inspired synthesis of oxindoles by catalytic aerobic dual C-H functionalization of phenols.

Authors:  Zheng Huang; Mohammad S Askari; Kenneth Virgel N Esguerra; Tian-Yang Dai; Ohhyeon Kwon; Xavier Ottenwaelder; Jean-Philip Lumb
Journal:  Chem Sci       Date:  2015-10-06       Impact factor: 9.825

  10 in total

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