Literature DB >> 31353817

Ligand-Enabled PdII -Catalyzed Iterative γ-C(sp3)-H Arylation of Free Aliphatic Acid.

Pravas Dolui1, Jayabrata Das1, Hediyala B Chandrashekar1, S S Anjana1, Debabrata Maiti1.   

Abstract

C-H functionalization of aliphatic carboxylic acids without attaching exogenous auxiliary has been so far limited at the proximal β-position. In this work, we demonstrate a ligand enabled palladium catalyzed first regioselective distal γ-C(sp3)-H functionalization of aliphatic carboxylic acids without incorporating an exogenous directing group. Aryl iodides containing versatile functional groups including complex organic molecules are well tolerated with good to excellent yields during the γ-C(sp3)-H arylation reaction. Interestingly, weak coordination of carboxylate group can be further extended for sequential hetero di-arylation. Application of the protocol has been showcased by synthesizing substituted α-tetralone. Mechanistic investigations have been carried out to shed light on the reaction pathway.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  iterative arylation; mechanistic studies; natural product incorporation; α-tetralone synthesis; γ-arylation

Year:  2019        PMID: 31353817     DOI: 10.1002/anie.201907262

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


  10 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

Review 3.  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

4.  Catalytic Behavior of Mono-N-Protected Amino-Acid Ligands in Ligand-Accelerated C-H Activation by Palladium(II).

Authors:  Chase A Salazar; Joseph J Gair; Kaylin N Flesch; Ilia A Guzei; Jared C Lewis; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-08       Impact factor: 15.336

Review 5.  Traditional and sustainable approaches for the construction of C-C bonds by harnessing C-H arylation.

Authors:  Jagrit Grover; Gaurav Prakash; Nupur Goswami; Debabrata Maiti
Journal:  Nat Commun       Date:  2022-02-28       Impact factor: 14.919

Review 6.  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

7.  Peptide late-stage C(sp3)-H arylation by native asparagine assistance without exogenous directing groups.

Authors:  Yiyi Weng; Xingxing Ding; João C A Oliveira; Xiaobin Xu; Nikolaos Kaplaneris; Meijie Zhu; Hantao Chen; Zhuo Chen; Lutz Ackermann
Journal:  Chem Sci       Date:  2020-08-12       Impact factor: 9.825

8.  Temperature-modulated selective C(sp3)-H or C(sp2)-H arylation through palladium catalysis.

Authors:  Thirupathi Gogula; Jinquan Zhang; Madhava Reddy Lonka; Shuaizhong Zhang; Hongbin Zou
Journal:  Chem Sci       Date:  2020-09-24       Impact factor: 9.825

9.  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 10.  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

  10 in total

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