Literature DB >> 23373630

Direct ortho-arylation of ortho-substituted benzoic acids: overriding Pd-catalyzed protodecarboxylation.

Carlos Arroniz1, Alan Ironmonger, Gerry Rassias, Igor Larrosa.   

Abstract

ortho-Arylation of ortho-substituted benzoic acids is a challenging process due to the tendency of the reaction products toward Pd-catalyzed protodecarboxylation. A simple method for preventing decarboxylation in sterically hindered benzoic acids is reported. The method described represents a reliable and broadly applicable entry to 2-aryl-6-substituted benzoic acids.

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Year:  2013        PMID: 23373630     DOI: 10.1021/ol400065j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  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

2.  Monoselective o-C-H Functionalizations of Mandelic Acid and α-Phenylglycine.

Authors:  Navid Dastbaravardeh; Tetsuya Toba; Marcus E Farmer; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-07-30       Impact factor: 15.419

3.  Tuning reactivity and site selectivity of simple arenes in C-H activation: ortho-arylation of anisoles via arene-metal π-complexation.

Authors:  Paolo Ricci; Katrina Krämer; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2014-12-16       Impact factor: 15.419

4.  Ruthenium-Catalyzed C-H Arylation of Diverse Aryl Carboxylic Acids with Aryl and Heteroaryl Halides.

Authors:  Liangbin Huang; Daniel J Weix
Journal:  Org Lett       Date:  2016-10-13       Impact factor: 6.005

5.  A Domino Oxidation/Arylation/Protodecarboxylation Reaction of Salicylaldehydes: Expanded Access to meta-Arylphenols.

Authors:  Junfei Luo; Sara Preciado; Solomon Olatokunbo Araromi; Igor Larrosa
Journal:  Chem Asian J       Date:  2015-06-25

6.  Ruthenium-Catalyzed C-H Arylation of Benzoic Acids and Indole Carboxylic Acids with Aryl Halides.

Authors:  Marco Simonetti; Diego M Cannas; Adyasha Panigrahi; Szymon Kujawa; Michal Kryjewski; Pan Xie; Igor Larrosa
Journal:  Chemistry       Date:  2016-12-05       Impact factor: 5.236

7.  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

Review 8.  Pd-catalysed C-H functionalisation of free carboxylic acids.

Authors:  Suparna Dutta; Trisha Bhattacharya; Finn J Geffers; Marcel Bürger; Debabrata Maiti; Daniel B Werz
Journal:  Chem Sci       Date:  2022-01-10       Impact factor: 9.825

9.  Ruthenium-Catalyzed Peri- and Ortho-Alkynylation with Bromoalkynes via Insertion and Elimination.

Authors:  Eric Tan; Andrey I Konovalov; Gabriela A Fernández; Ruth Dorel; Antonio M Echavarren
Journal:  Org Lett       Date:  2017-10-04       Impact factor: 6.005

  9 in total

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