Literature DB >> 24706602

Palladium-catalyzed C(sp(3))-H activation: a facile method for the synthesis of 3,4-dihydroquinolinone derivatives.

Jia-Xuan Yan1, Hu Li, Xiang-Wei Liu, Jiang-Ling Shi, Xin Wang, Zhang-Jie Shi.   

Abstract

3,4-Dihydroquinolinones were synthesized by the palladium-catalyzed, oxidative-addition-initiated activation and arylation of inert C(sp(3) )H bonds. Pd(OAc)2 and P(o-tol)3 were used as the catalyst and ligand, respectively, to improve the efficiency of the reaction. A further advantage of this reaction is that it could be performed in air. A relatively rare seven-membered palladacycle was proposed as a key intermediate of the catalytic cycle.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; dihydroquinolinones; palladacycles; palladium; synthetic methods

Mesh：

Substances：

Year:  2014        PMID： 24706602     DOI： 10.1002/anie.201402562

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

Review 1.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

2.  Enantioselective palladium(0)-catalyzed intramolecular cyclopropane functionalization: access to dihydroquinolones, dihydroisoquinolones and the BMS-791325 ring system.

Authors:  J Pedroni; T Saget; P A Donets; N Cramer
Journal:  Chem Sci       Date:  2015-06-17       Impact factor: 9.825

3.  Palladium(0)-catalyzed asymmetric C(sp3)-H arylation using a chiral binol-derived phosphate and an achiral ligand.

Authors:  Lei Yang; Romain Melot; Markus Neuburger; Olivier Baudoin
Journal:  Chem Sci       Date:  2016-10-11       Impact factor: 9.825

4.  C(sp3 )-H Arylation Promoted by a Heterogeneous Palladium-N-Heterocyclic Carbene Complex in Batch and Continuous Flow.

Authors:  Francesco Ferlin; Ioannis Anastasiou; Nihad Salameh; Takeru Miyakoshi; Olivier Baudoin; Luigi Vaccaro
Journal:  ChemSusChem       Date:  2022-02-18       Impact factor: 9.140

5.  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

6.  Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp3)-H bonds of aliphatic amine substrates.

Authors:  Chao Wang; Li Zhang; Changpeng Chen; Jian Han; Yingming Yao; Yingsheng Zhao
Journal:  Chem Sci       Date:  2015-05-19       Impact factor: 9.825

7.  Modular synthesis of dihydro-isoquinolines: palladium-catalyzed sequential C(sp2)-H and C(sp3)-H bond activation.

Authors:  Weidong Liu; Qingzhen Yu; Le'an Hu; Zenghua Chen; Jianhui Huang
Journal:  Chem Sci       Date:  2015-06-26       Impact factor: 9.825
  7 in total

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