Literature DB >> 28492623

The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation.

Marc Font1, Jacob M Quibell1, Gregory J P Perry1, Igor Larrosa1.   

Abstract

The ability to selectively functionalise a specific C-H bond is a long-standing challenge due to the ubiquity of such bonds in organic molecules. One of the most common approaches to overcome this obstacle consists of installing directing groups into substrates to direct the functionalisation towards the desired C-H bond, leaving behind the directing group in the molecule. Alternatively, carboxylic acids have been employed as traceless directing groups that are easily removed after carboxylic acid-directed installation of the desired functionality. This review focuses on the development of this concept and its application to organic synthesis during the last decade.

Entities:  

Year:  2017        PMID: 28492623     DOI: 10.1039/c7cc01755c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  14 in total

1.  Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-10       Impact factor: 15.336

2.  Catalytic Alkyne Arylation Using Traceless Directing Groups.

Authors:  Jung-Woo Park; Bubwoong Kang; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-11       Impact factor: 15.336

3.  Ruthenium-Catalyzed C-H Arylation of 1-Naphthol with Aryl and Heteroaryl Halides.

Authors:  Amanda M Spiewak; Daniel J Weix
Journal:  J Org Chem       Date:  2019-11-25       Impact factor: 4.354

4.  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

5.  meta-Selective C-H Arylation of Fluoroarenes and Simple Arenes.

Authors:  Luo-Yan Liu; Jennifer X Qiao; Kap-Sun Yeung; William R Ewing; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-09       Impact factor: 15.336

Review 6.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

7.  Palladium catalysed C-H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions.

Authors:  Xavier Just-Baringo; Yuyoung Shin; Adyasha Panigrahi; Marco Zarattini; Vaiva Nagyte; Ling Zhao; Kostas Kostarelos; Cinzia Casiraghi; Igor Larrosa
Journal:  Chem Sci       Date:  2020-01-28       Impact factor: 9.825

Review 8.  C4-H indole functionalisation: precedent and prospects.

Authors:  Jagadeesh Kalepu; Parthasarathy Gandeepan; Lutz Ackermann; Lukasz T Pilarski
Journal:  Chem Sci       Date:  2018-04-20       Impact factor: 9.825

9.  Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.

Authors:  Gregory J P Perry; Jacob M Quibell; Adyasha Panigrahi; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2017-08-08       Impact factor: 15.419

10.  meta-C-H arylation of fluoroarenes via traceless directing group relay strategy.

Authors:  Marc Font; Andrew R A Spencer; Igor Larrosa
Journal:  Chem Sci       Date:  2018-07-25       Impact factor: 9.825

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