Literature DB >> 27786439

Pd-Catalyzed γ-C(sp3)-H Arylation of Free Amines Using a Transient Directing Group.

Yongwei Wu1, Yan-Qiao Chen1, Tao Liu1, Martin D Eastgate2, Jin-Quan Yu.   

Abstract

Pd(II)-catalyzed γ-C(sp3)-H arylation of primary amines is realized by using 2-hydroxynicotinaldehyde as a catalytic transient directing group. Importantly, the catalyst and the directing group loading can be lowered to 2% and 4% respectively, thus demonstrating high efficiency of this newly designed transient directing group. Heterocyclic aryl iodides are also compatible with this reaction. Furthermore, swift synthesis of 1,2,3,4-tetrahydronaphthyridine derivatives is accomplished using this reaction.

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Year:  2016        PMID： 27786439      PMCID： PMC5535771          DOI： 10.1021/jacs.6b09653

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


  41 in total

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2.  Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

3.  Palladium-catalyzed direct functionalization of 2-aminobutanoic acid derivatives: application of a convenient and versatile auxiliary.

Authors:  Mengyang Fan; Dawei Ma
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-23       Impact factor: 15.336

4.  The catalytic intermolecular orthoarylation of phenols.

Authors:  Robin B Bedford; Simon J Coles; Michael B Hursthouse; Michael E Limmert
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-03       Impact factor: 15.336

5.  Catalytic C(sp(3) )-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ.

Authors:  Yan Xu; Michael C Young; Chengpeng Wang; David M Magness; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-08       Impact factor: 15.336

6.  C-H bond activation. Regioselective ketone α-alkylation with simple olefins via dual activation.

Authors:  Fanyang Mo; Guangbin Dong
Journal:  Science       Date:  2014-07-04       Impact factor: 47.728

7.  Ruthenium(II)-catalyzed C-H bond activation and functionalization.

Authors:  Percia Beatrice Arockiam; Christian Bruneau; Pierre H Dixneuf
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

8.  Expanding the scope of C-H amination through catalyst design.

Authors:  Christine G Espino; Kristin Williams Fiori; Mihyong Kim; J Du Bois
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

9.  Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group.

Authors:  Fang-Lin Zhang; Kai Hong; Tuan-Jie Li; Hojoon Park; Jin-Quan Yu
Journal:  Science       Date:  2016-01-15       Impact factor: 47.728

Review 10.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors:  Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  32 in total

1.  Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Authors:  Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal:  Synlett       Date:  2019-11-27       Impact factor: 2.454

2.  Enantioselective γ-C(sp3)-H Activation of Alkyl Amines via Pd(II)/Pd(0) Catalysis.

Authors:  Qian Shao; Qing-Feng Wu; Jian He; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2018-04-11       Impact factor: 15.419

3.  Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source.

Authors:  Mohit Kapoor; Pratibha Chand-Thakuri; Justin M Maxwell; Michael C Young
Journal:  J Vis Exp       Date:  2018-08-17       Impact factor: 1.355

4.  Pd-Catalyzed γ-C(sp3)-H Fluorination of Free Amines.

Authors:  Yan-Qiao Chen; Sukriti Singh; Yongwei Wu; Zhen Wang; Wei Hao; Pritha Verma; Jennifer X Qiao; Raghavan B Sunoj; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-05-18       Impact factor: 15.419

Review 5.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

6.  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

7.  Methylene C(sp3)-H Arylation of Aliphatic Ketones Using a Transient Directing Group.

Authors:  Kai Hong; Hojoon Park; Jin-Quan Yu
Journal:  ACS Catal       Date:  2017-09-13       Impact factor: 13.084

8.  Remote, Late-Stage Oxidation of Aliphatic C-H Bonds in Amide-Containing Molecules.

Authors:  Takeshi Nanjo; Emilio C de Lucca; M Christina White
Journal:  J Am Chem Soc       Date:  2017-10-04       Impact factor: 15.419

9.  Iridium-Catalyzed, β-Selective C(sp3)-H Silylation of Aliphatic Amines To Form Silapyrrolidines and 1,2-Amino Alcohols.

Authors:  Bo Su; Taegyo Lee; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-12-13       Impact factor: 15.419

10.  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
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