Literature DB >> 26313012

Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene.

Peng-Xiang Shen1, Xiao-Chen Wang1, Peng Wang1, Ru-Yi Zhu1, Jin-Quan Yu1.   

Abstract

2-Carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd(II)-catalyzed meta-C(sp(2))-H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for this reaction to proceed.

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Year:  2015        PMID： 26313012      PMCID： PMC4573956          DOI： 10.1021/jacs.5b08914

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  55 in total

1.  Palladium-catalyzed alkylation-hydride reduction sequence: synthesis of meta-substituted arenes.

Authors:  Thorsten Wilhelm; Mark Lautens
Journal:  Org Lett       Date:  2005-09-01       Impact factor: 6.005

2.  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

3.  A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction.

Authors:  Cyril Bressy; Dino Alberico; Mark Lautens
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

4.  Cobalt-catalyzed ortho-alkylation of secondary benzamide with alkyl chloride through directed C-H bond activation.

Authors:  Quan Chen; Laurean Ilies; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2010-12-15       Impact factor: 15.419

5.  Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol.

Authors:  Chen Cheng; John F Hartwig
Journal:  Science       Date:  2014-02-21       Impact factor: 47.728

6.  Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance.

Authors:  Yoshinori Aihara; Naoto Chatani
Journal:  J Am Chem Soc       Date:  2013-04-01       Impact factor: 15.419

7.  meta-Selective C-H bond alkylation with secondary alkyl halides.

Authors:  Nora Hofmann; Lutz Ackermann
Journal:  J Am Chem Soc       Date:  2013-04-08       Impact factor: 15.419

8.  Ligand-enabled meta-C-H activation using a transient mediator.

Authors:  Xiao-Chen Wang; Wei Gong; Li-Zhen Fang; Ru-Yi Zhu; Suhua Li; Keary M Engle; Jin-Quan Yu
Journal:  Nature       Date:  2015-03-09       Impact factor: 49.962

9.  A new reaction sequence involving palladium-catalyzed unsymmetrical aryl coupling.

Authors:  Fiorenza Faccini; Elena Motti; Marta Catellani
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419

10.  Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides.

Authors:  Ke Gao; Naohiko Yoshikai
Journal:  J Am Chem Soc       Date:  2013-06-17       Impact factor: 15.419
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  35 in total

1.  meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2019-09-06       Impact factor: 15.419

2.  Palladium/Norbornene Cooperative Catalysis.

Authors:  Jianchun Wang; Guangbin Dong
Journal:  Chem Rev       Date:  2019-04-25       Impact factor: 60.622

3.  Ligand-Enabled Auxiliary-Free meta-C-H Arylation of Phenylacetic Acids.

Authors:  Gen-Cheng Li; Peng Wang; Marcus E Farmer; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-09       Impact factor: 15.336

4.  Palladium-catalyzed asymmetric annulation between aryl iodides and racemic epoxides using a chiral norbornene cocatalyst.

Authors:  Renhe Li; Feipeng Liu; Guangbin Dong
Journal:  Org Chem Front       Date:  2018-09-25       Impact factor: 5.281

5.  Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis.

Authors:  Renhe Li; Yun Zhou; Xiaolong Xu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2019-11-22       Impact factor: 15.419

6.  Distal Alkenyl C-H Functionalization via the Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhao Wu; Nina Fatuzzo; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2020-02-03       Impact factor: 15.419

7.  Palladium/Norbornene-Catalyzed Indenone Synthesis from Simple Aryl Iodides: Concise Syntheses of Pauciflorol F and Acredinone A.

Authors:  Feipeng Liu; Zhe Dong; Jianchun Wang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-16       Impact factor: 15.336

8.  meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.

Authors:  Guolin Cheng; Peng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-09       Impact factor: 15.336

9.  Modular ipso/ ortho Difunctionalization of Aryl Bromides via Palladium/Norbornene Cooperative Catalysis.

Authors:  Zhe Dong; Gang Lu; Jianchun Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2018-06-27       Impact factor: 15.419

10.  Ligand-Promoted C(sp(3) )-H Olefination en Route to Multi-functionalized Pyrazoles.

Authors:  Weibo Yang; Shengqing Ye; Yvonne Schmidt; Dean Stamos; Jin-Quan Yu
Journal:  Chemistry       Date:  2016-04-15       Impact factor: 5.236
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