Literature DB >> 28371173

Ligand-Promoted meta-C-H Functionalization of Benzylamines.

Peng Wang1, Marcus E Farmer1, Jin-Quan Yu1.   

Abstract

Meta-C-H functionalization of benzylamines has been developed using a PdII /transient mediator strategy. Using 2-pyridone ligands and 2-carbomethoxynorbornene (NBE-CO2 Me) as the mediator, arylation, amination, and chlorination of benzylamines are realized. This protocol features a broad substrate scope and is compatible with heterocylic coupling partners. Moreover, the loading of the Pd can be lowered to 2.5 mol % by using the optimal ligand.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; benzylamines; chlorination; meta-C−H arylation; pyridone ligand

Mesh：

Substances：

Year:  2017        PMID： 28371173      PMCID： PMC5512280          DOI： 10.1002/anie.201701803

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


  38 in total

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2.  Pd(II)-catalyzed ortho-trifluoromethylation of benzylamines.

Authors:  Masanori Miura; Chen-Guo Feng; Sandy Ma; Jin-Quan Yu
Journal:  Org Lett       Date:  2013-10-07       Impact factor: 6.005

3.  Simple Amine-Directed Meta-Selective C-H Arylation via Pd/Norbornene Catalysis.

Authors:  Zhe Dong; Jianchun Wang; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2015-04-28       Impact factor: 15.419

4.  Transition metal catalyzed meta-C-H functionalization of aromatic compounds.

Authors:  Jiong Yang
Journal:  Org Biomol Chem       Date:  2015-02-21       Impact factor: 3.876

5.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal:  Science       Date:  2001-11-22       Impact factor: 47.728

6.  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

7.  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

8.  Enantioselective ortho-C-H cross-coupling of diarylmethylamines with organoborons.

Authors:  Brian N Laforteza; Kelvin S L Chan; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-04       Impact factor: 15.336

9.  Ligand-Enabled meta-Selective C-H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines.

Authors:  Qiuping Ding; Shengqing Ye; Guolin Cheng; Peng Wang; Marcus E Farmer; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2016-12-23       Impact factor: 15.419

10.  Palladium-catalysed norbornene-mediated C-H functionalization of arenes.

Authors:  Juntao Ye; Mark Lautens
Journal:  Nat Chem       Date:  2015-11       Impact factor: 24.427
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  14 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.  Enantioselective remote meta-C-H arylation and alkylation via a chiral transient mediator.

Authors:  Hang Shi; Alastair N Herron; Ying Shao; Qian Shao; Jin-Quan Yu
Journal:  Nature       Date:  2018-06-18       Impact factor: 49.962

4.  PdII-Catalyzed Site-selective β- and γ-C(sp3)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

Authors:  Yi-Hao Li; Yuxin Ouyang; Nikita Chekshin; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2022-03-14       Impact factor: 16.383

5.  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

6.  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

7.  Ligand-Enabled γ-C(sp3)-H Activation of Ketones.

Authors:  Ru-Yi Zhu; Zi-Qi Li; Han Seul Park; Chris H Senanayake; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2018-03-02       Impact factor: 15.419

8.  Ligand-Enabled Pd(II)-Catalyzed C(sp3)-H Lactonization Using Molecular Oxygen as Oxidant.

Authors:  Shaoqun Qian; Zi-Qi Li; Minyan Li; Steven R Wisniewski; Jennifer X Qiao; Jeremy M Richter; William R Ewing; Martin D Eastgate; Jason S Chen; Jin-Quan Yu
Journal:  Org Lett       Date:  2020-04-24       Impact factor: 6.005

9.  Meta-Selective C-H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold.

Authors:  Qiankun Li; Eric M Ferreira
Journal:  Chemistry       Date:  2017-08-07       Impact factor: 5.236

10.  Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.

Authors:  Yu-Jie Wang; Chen-Hui Yuan; De-Zhao Chu; Lei Jiao
Journal:  Chem Sci       Date:  2020-09-23       Impact factor: 9.825
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