Literature DB >> 29148233

Pd-Catalyzed β-C(sp3 )-H Arylation of Propionic Acid and Related Aliphatic Acids.

Kiron K Ghosh1, Manuel van Gemmeren1,2.   

Abstract

A generally applicable Pd-catalyzed protocol for the β-C(sp3 )-H arylation of propionic acid and related α-branched aliphatic acids is reported. Enabled by the use of N-acetyl-β-alanine as ligand our protocol delivers a broad range of arylation products. Notably, the highly challenging substrate, propionic acid, which lacks any acceleration through the Thorpe-Ingold effect, can be employed as substrate with synthetically useful yields. Furthermore, the scalability and synthetic applicability of the protocol are demonstrated.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; arylation; carboxylic acids; palladium; propionic acid

Year:  2017        PMID: 29148233     DOI: 10.1002/chem.201705449

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  14 in total

1.  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

2.  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

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

Authors:  Zhe Zhuang; Chang-Bin Yu; Gang Chen; Qing-Feng Wu; Yi Hsiao; Candice L Joe; Jennifer X Qiao; Michael A Poss; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2018-08-02       Impact factor: 15.419

4.  From Pd(OAc)2 to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.

Authors:  Qian Shao; Kevin Wu; Zhe Zhuang; Shaoqun Qian; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2020-03-31       Impact factor: 22.384

5.  Ligand-Enabled Monoselective β-C(sp3)-H Acyloxylation of Free Carboxylic Acids Using a Practical Oxidant.

Authors:  Zhe Zhuang; Alastair N Herron; Zhoulong Fan; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-03-30       Impact factor: 15.419

6.  Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Free Carboxylic Acids.

Authors:  Peng-Xiang Shen; Liang Hu; Qian Shao; Kai Hong; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2018-05-17       Impact factor: 15.419

Review 7.  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

8.  Synthesis of Cyclic Anhydrides via Ligand-Enabled C-H Carbonylation of Simple Aliphatic Acids.

Authors:  Zhe Zhuang; Alastair N Herron; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

9.  Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F.

Authors:  Zhe Zhuang; Alastair N Herron; Shuang Liu; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2021-01-04       Impact factor: 15.419

10.  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

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