Literature DB >> 32250014

Ligand-Enabled γ-C(sp3)-H Olefination of Free Carboxylic Acids.

Kiron Kumar Ghosh1, Alexander Uttry1, Arup Mondal2, Francesca Ghiringhelli3, Philipp Wedi2, Manuel van Gemmeren4.   

Abstract

We report the ligand enabled C-H activation/olefination of free carboxylic acids in the γ-position. Through an intramolecular Michael-addition, δ-lactones are obtained as products. Two distinct ligand classes are identified that enable the challenging palladium-catalyzed activation of free carboxylic acids in the γ-position. The developed protocol features a wide range of acid substrates and olefin reaction partners and is shown to be applicable on a preparatively useful scale. Insights into the underlying reaction mechanism obtained through kinetic studies are reported.
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Ligand-Enabled Catalysis; Palladium; carboxylic acids; γ-C(sp3)-H activation; δ-Lactones

Year:  2020        PMID： 32250014     DOI： 10.1002/anie.202002362

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Distal γ-C(sp3 )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

Authors:  Han Seul Park; Zhoulong Fan; Ru-Yi Zhu; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

Review 2.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

3.  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

Review 4.  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

5.  Tailored quinones support high-turnover Pd catalysts for oxidative C-H arylation with O2.

Authors:  Chase A Salazar; Kaylin N Flesch; Brandon E Haines; Philip S Zhou; Djamaladdin G Musaev; Shannon S Stahl
Journal:  Science       Date:  2020-11-19       Impact factor: 47.728

6.  A direct route to six and seven membered lactones via γ-C(sp3)-H activation: a simple protocol to build molecular complexity.

Authors:  Jayabrata Das; Pravas Dolui; Wajid Ali; Jyoti Prasad Biswas; Hediyala B Chandrashekar; Gaurav Prakash; Debabrata Maiti
Journal:  Chem Sci       Date:  2020-08-19       Impact factor: 9.825

Review 7.  Diverse strategies for transition metal catalyzed distal C(sp3)-H functionalizations.

Authors:  Jayabrata Das; Srimanta Guin; Debabrata Maiti
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

Review 8.  Transition-Metal-Catalyzed Annulations Involving the Activation of C(sp3 )-H Bonds.

Authors:  Marc Font; Moisés Gulías; José Luis Mascareñas
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-02       Impact factor: 16.823
  8 in total

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