Literature DB >> 30581651

Palladium Catalyzed meta-C-H Functionalization of Masked Aromatic Aldehydes.

Marcus E Farmer1, Peng Wang1, Hang Shi1, Jin-Quan Yu1.   

Abstract

Palladium catalyzed meta-C-H functionalization enabled by transient mediators has the potential to extend the utility of directed ortho-C-H functionalization to remote positions. However, there have been no reports of palladium catalyzed meta-C-H functionalization of aromatic aldehyde derivatives, which are highly versatile intermediates in organic synthesis. Herein we report the development of a directing group that, in the presence of a norbornene derived mediator and an appropriate pyridone ligand, allows palladium catalyzed meta-C-H functionalization of masked aromatic aldehydes. Mechanistic insight regarding the impact of the directing group length on this catalysis is also discussed.

Entities:  

Keywords:  Aryl-Aldehyde; Benzaldehyde; C-H Activation; Meta-C–H Activation; Palladium; Pyridone Ligand

Year:  2018        PMID： 30581651      PMCID： PMC6301045          DOI： 10.1021/acscatal.8b01599

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  10 in total

1.  Pd-Catalyzed γ-C(sp3)-H Fluorination of Free Amines.

Authors:  Yan-Qiao Chen; Sukriti Singh; Yongwei Wu; Zhen Wang; Wei Hao; Pritha Verma; Jennifer X Qiao; Raghavan B Sunoj; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-05-18       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.  RhodiumIII-catalyzed remote difunctionalization of arenes assisted by a relay directing group.

Authors:  Lincong Sun; Yuyao Zhao; Bingxian Liu; Junbiao Chang; Xingwei Li
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

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.  Ligand Enabled Pd(II)-Catalyzed γ-C(sp3)-H Lactamization of Native Amides.

Authors:  Shuang Liu; Zhe Zhuang; Jennifer X Qiao; Kap-Sun Yeung; Shun Su; Emily C Cherney; Zheming Ruan; William R Ewing; Michael A Poss; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2021-12-16       Impact factor: 16.383

6.  PdII -Catalyzed Enantioselective C(sp3 )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

Authors:  Li-Jun Xiao; Kai Hong; Fan Luo; Liang Hu; William R Ewing; Kap-Sun Yeung; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-01       Impact factor: 15.336

7.  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

8.  Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups.

Authors:  Jin-Tang Cheng; Li-Jun Xiao; Shao-Qun Qian; Zhe Zhuang; An Liu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-09       Impact factor: 16.823

9.  Imine as a linchpin approach for meta-C-H functionalization.

Authors:  Sukdev Bag; Sadhan Jana; Sukumar Pradhan; Suman Bhowmick; Nupur Goswami; Soumya Kumar Sinha; Debabrata Maiti
Journal:  Nat Commun       Date:  2021-03-02       Impact factor: 14.919

10.  Recyclable Ruthenium Catalyst for Distal meta-C-H Activation.

Authors:  Isaac Choi; Valentin Müller; Yanhui Wang; Kai Xue; Rositha Kuniyil; Loren B Andreas; Volker Karius; Johan G Alauzun; Lutz Ackermann
Journal:  Chemistry       Date:  2020-10-22       Impact factor: 5.236
  10 in total

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