Literature DB >> 29796566

Transient imines as 'next generation' directing groups for the catalytic functionalisation of C-H bonds in a single operation.

Sahra St John-Campbell1, James A Bull1.   

Abstract

C-H functionalisation promises a paradigm shift in synthetic planning. However, the additional steps often required to install and remove directing groups currently detract from the efficiency. The strategy of reversible installation of a directing group via an imine linkage has recently emerged, with the imine formed and hydrolysed in situ. Such transient directing groups can promote transition metal catalysed functionalisation of unactivated C-H bonds of aldehydes, ketones and amines. This approach removes additional steps usually required for covalent directing groups and can use catalytic quantities of the imine forming component. This review updates the rapidly developing field of transient directing groups for C-H functionalisation on sp2 and sp3 carbon centres, to form new C-C and C-X bonds. We focus on the structures of the transient directing groups as mono or bidentate coordinating groups for various metal catalysts.

Entities:  

Year:  2018        PMID: 29796566     DOI: 10.1039/c8ob00926k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  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.  Transient Directing Group Enabled Pd-catalyzed γ-C(sp3)-H Oxygenation of Alkyl Amines.

Authors:  Yan-Qiao Chen; Yongwei Wu; Zhen Wang; Jennifer X Qiao; Jin-Quan Yu
Journal:  ACS Catal       Date:  2020-04-24       Impact factor: 13.084

3.  Transient directing group enabled Pd-catalyzed C-H oxygenation of benzaldehydes and benzylic amines.

Authors:  Mixiang Tian; Lidong Shao; Xiaosan Su; Xuhong Zhou; Honglei Zhang; Kun Wei; Ruifen Sun; Junliang Wang
Journal:  RSC Adv       Date:  2022-06-27       Impact factor: 4.036

4.  Amine-Catalyzed Copper-Mediated C-H Sulfonylation of Benzaldehydes via a Transient Imine Directing Group.

Authors:  Joe I Higham; James A Bull
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-05       Impact factor: 16.823

5.  Ligand-promoted palladium-catalyzed β-methylene C-H arylation of primary aldehydes.

Authors:  Ke Yang; Zhi Li; Chong Liu; Yunjian Li; Qingyue Hu; Mazen Elsaid; Bijin Li; Jayabrata Das; Yanfeng Dang; Debabrata Maiti; Haibo Ge
Journal:  Chem Sci       Date:  2022-04-25       Impact factor: 9.969

6.  A Transient-Directing-Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes.

Authors:  Lucas J Oxtoby; Zi-Qi Li; Van T Tran; Tuğçe G Erbay; Ruohan Deng; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-07       Impact factor: 15.336

Review 7.  Transition-metal-catalyzed remote C-H functionalization of thioethers.

Authors:  Xiao-Qing Feng; He-Cheng Wang; Zhi Li; Long Tang; Xiaoqiang Sun; Ke Yang
Journal:  RSC Adv       Date:  2022-04-07       Impact factor: 3.361

Review 8.  Aldehyde catalysis - from simple aldehydes to artificial enzymes.

Authors:  Zeqin Yuan; Jun Liao; Hao Jiang; Peng Cao; Yang Li
Journal:  RSC Adv       Date:  2020-09-25       Impact factor: 4.036

9.  Access to indolines from primary phenylethylamines by an unexpected palladium-catalyzed C-H functionalization process.

Authors:  Andrea Mancinelli; Joan Albert; Xavier Ariza; Leoní A Barrios; Jordi Garcia; Roberto Gómez; Jaume Granell
Journal:  RSC Adv       Date:  2019-08-29       Impact factor: 4.036

10.  Palladium-Catalyzed C(sp3 )-H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group.

Authors:  Sahra St John-Campbell; Alex K Ou; James A Bull
Journal:  Chemistry       Date:  2018-11-08       Impact factor: 5.236

  10 in total

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