Literature DB >> 29741883

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

Peng-Xiang Shen1, Liang Hu1, Qian Shao1, Kai Hong1, Jin-Quan Yu1.   

Abstract

A monoprotected aminoethyl amine chiral ligand based on an ethylenediamine backbone was developed to achieve Pd-catalyzed enantioselective C(sp3)-H arylation of cyclopropanecarboxylic and 2-aminoisobutyric acids without using exogenous directing groups. This new chiral catalyst affords new disconnection for preparing diverse chiral carboxylic acids from simple starting materials that are complementary to the various ring forming approaches.

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Year:  2018        PMID: 29741883      PMCID: PMC6038808          DOI: 10.1021/jacs.8b03509

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  29 in total

Review 1.  Protecting-group-free synthesis as an opportunity for invention.

Authors:  Ian S Young; Phil S Baran
Journal:  Nat Chem       Date:  2009-06       Impact factor: 24.427

2.  Fused indolines by palladium-catalyzed asymmetric C-C coupling involving an unactivated methylene group.

Authors:  Masafumi Nakanishi; Dmitry Katayev; Céline Besnard; E Peter Kündig
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-01       Impact factor: 15.336

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

Authors:  Kiron K Ghosh; Manuel van Gemmeren
Journal:  Chemistry       Date:  2017-11-30       Impact factor: 5.236

4.  Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.

Authors:  Masayuki Wasa; Keary M Engle; David W Lin; Eun Jeong Yoo; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-11-21       Impact factor: 15.419

5.  Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis.

Authors:  Yong Wang; Xin Wen; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2017-01-12       Impact factor: 15.419

6.  In situ generation of zinc carbenoids from diazo compounds and zinc salts: asymmetric synthesis of 1,2,3-substituted cyclopropanes.

Authors:  Sébastien R Goudreau; André B Charette
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

7.  The "Cyclopropyl Fragment" is a Versatile Player that Frequently Appears in Preclinical/Clinical Drug Molecules.

Authors:  Tanaji T Talele
Journal:  J Med Chem       Date:  2016-06-30       Impact factor: 7.446

8.  Rhodium-Catalyzed Enantioselective Silylation of Cyclopropyl C-H Bonds.

Authors:  Taegyo Lee; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-02       Impact factor: 15.336

9.  Access to Cyclopropyl-Fused Azacycles via a Palladium-Catalyzed Direct Alkenylation Strategy.

Authors:  Carolyn L Ladd; André B Charette
Journal:  Org Lett       Date:  2016-11-14       Impact factor: 6.005

10.  Pd-catalysed ligand-enabled carboxylate-directed highly regioselective arylation of aliphatic acids.

Authors:  Yan Zhu; Xiaolan Chen; Chunchen Yuan; Guobao Li; Jingyu Zhang; Yingsheng Zhao
Journal:  Nat Commun       Date:  2017-04-06       Impact factor: 14.919

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  28 in total

1.  Pd(II)-Catalyzed Enantioselective γ-C(sp3)-H Functionalizations of Free Cyclopropylmethylamines.

Authors:  Zhe Zhuang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-07-07       Impact factor: 15.419

2.  PdII -Catalyzed Enantioselective C(sp3 )-H Activation/Cross-Coupling Reactions of Free Carboxylic Acids.

Authors:  Liang Hu; Peng-Xiang Shen; Qian Shao; Kai Hong; Jennifer X Qiao; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-16       Impact factor: 15.336

3.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

4.  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

5.  Rhodium-Catalyzed Asymmetric Hydroamination of Allyl Amines.

Authors:  Evan P Vanable; Jennifer L Kennemur; Leo A Joyce; Rebecca T Ruck; Danielle M Schultz; Kami L Hull
Journal:  J Am Chem Soc       Date:  2019-01-07       Impact factor: 15.419

6.  PdII -Catalyzed Enantioselective C(sp3 )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

Authors:  Li-Jun Xiao; Kai Hong; Fan Luo; Liang Hu; William R Ewing; Kap-Sun Yeung; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-01       Impact factor: 15.336

7.  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

8.  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

9.  Directed, Palladium(II)-Catalyzed Enantioselective anti-Carboboration of Alkenyl Carbonyl Compounds.

Authors:  Zhen Liu; Xiaohan Li; Tian Zeng; Keary M Engle
Journal:  ACS Catal       Date:  2019-03-13       Impact factor: 13.084

10.  Ligand-Enabled Pd(II)-Catalyzed C(sp3)-H Lactonization Using Molecular Oxygen as Oxidant.

Authors:  Shaoqun Qian; Zi-Qi Li; Minyan Li; Steven R Wisniewski; Jennifer X Qiao; Jeremy M Richter; William R Ewing; Martin D Eastgate; Jason S Chen; Jin-Quan Yu
Journal:  Org Lett       Date:  2020-04-24       Impact factor: 6.005

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