Literature DB >> 32926032

Transient imine directing groups for the C-H functionalisation of aldehydes, ketones and amines: an update 2018-2020.

Joe I Higham1, James A Bull1.   

Abstract

The use of pre-installed directing groups has become a popular and powerful strategy to control site selectivity in transition metal catalysed C-H functionalisation reactions. However, the necessity for directing group installation and removal reduces the efficiency of a directed C-H functionalisation method. To overcome this limitation, taking inspiration from organocatalytic methodologies, the use of transient directing groups has arisen. These methods allow for a transient ligand to be used, potentially in catalytic quantities, without the need for discrete installation or removal steps, enabling the discovery of more efficient, and mechanistically intriguing, dual catalytic methods. This review summarises recent developments in this fast moving field covering >70 new methodologies, highlighting new directing group designs and advances in mechanistic understanding. It covers progress since 2018, providing an update to our previous review of the field.

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Year:  2020        PMID: 32926032     DOI: 10.1039/d0ob01587c

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


  5 in total

1.  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

2.  A directing group switch in copper-catalyzed electrophilic C-H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole.

Authors:  Hasina Mamataj Begam; Shantanu Nandi; Ranjan Jana
Journal:  Chem Sci       Date:  2022-04-14       Impact factor: 9.969

3.  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

4.  PdII -Catalyzed C(alkenyl)-H Activation Facilitated by a Transient Directing Group.

Authors:  Mingyu Liu; Juntao Sun; Tuğçe G Erbay; Hui-Qi Ni; Raúl Martín-Montero; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-26       Impact factor: 16.823

5.  A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis.

Authors:  Zhonglin Liu; Lucas J Oxtoby; Mingyu Liu; Zi-Qi Li; Van T Tran; Yang Gao; Keary M Engle
Journal:  J Am Chem Soc       Date:  2021-06-02       Impact factor: 16.383

  5 in total

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