Literature DB >> 26990413

A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp(2) C-H Bond Amination.

James Roane1, Olafs Daugulis1.   

Abstract

An operationally simple and general method for copper-catalyzed, aminoquinoline-assisted amination of β-C(sp(2))-H bonds of benzoic acid derivatives is reported. The reaction employs Cu(OAc)2 or (CuOH)2CO3 catalysts, an amine coupling partner, and oxygen from air as a terminal oxidant. Exceptionally high generality with respect to amine coupling partners is observed. Specifically, primary and secondary aliphatic and aromatic amines, heterocycles, such as indoles, pyrazole, and carbazole, sulfonamides, as well as electron-deficient aromatic and heteroaromatic amines are competent coupling components.

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Year:  2016        PMID： 26990413      PMCID： PMC4829344          DOI： 10.1021/jacs.6b01117

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


  41 in total

1.  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

2.  Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

Authors:  Hung-Yat Thu; Wing-Yiu Yu; Chi-Ming Che
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

3.  Nickel-catalyzed direct amination of arenes with alkylamines.

Authors:  Qiangqiang Yan; Zhengkai Chen; Wenlong Yu; Hong Yin; Zhanxiang Liu; Yuhong Zhang
Journal:  Org Lett       Date:  2015-05-05       Impact factor: 6.005

4.  Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.

Authors:  Yajing Lian; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

5.  C-H nitrogenation and oxygenation by ruthenium catalysis.

Authors:  Vedhagiri S Thirunavukkarasu; Sergei I Kozhushkov; Lutz Ackermann
Journal:  Chem Commun (Camb)       Date:  2013-11-11       Impact factor: 6.222

6.  Sterically controlled, palladium-catalyzed intermolecular amination of arenes.

Authors:  Ruja Shrestha; Paramita Mukherjee; Yichen Tan; Zachary C Litman; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-05-28       Impact factor: 15.419

7.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

8.  Copper-mediated aromatic amination reaction and its application to the total synthesis of natural products.

Authors:  Kentaro Okano; Hidetoshi Tokuyama; Tohru Fukuyama
Journal:  Chem Commun (Camb)       Date:  2014-11-18       Impact factor: 6.222

9.  Expedient C-H amidations of heteroaryl arenes catalyzed by versatile ruthenium(II) catalysts.

Authors:  Vedhagiri S Thirunavukkarasu; Keshav Raghuvanshi; Lutz Ackermann
Journal:  Org Lett       Date:  2013-06-14       Impact factor: 6.005

10.  Direct C-H amination of arenes with alkyl azides under rhodium catalysis.

Authors:  Kwangmin Shin; Yunjung Baek; Sukbok Chang
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-20       Impact factor: 15.336
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  11 in total

1.  Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.

Authors:  Charles E Hendrick; Katie J Bitting; Seoyoung Cho; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

2.  A directing group switch in copper-catalyzed electrophilic C-H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole.

Authors:  Hasina Mamataj Begam; Shantanu Nandi; Ranjan Jana
Journal:  Chem Sci       Date:  2022-04-14       Impact factor: 9.969

3.  N-Aminopyridinium Ylide-Directed, Copper-Promoted Amination of sp2 C-H Bonds.

Authors:  Se Hun Kwak; Olafs Daugulis
Journal:  J Org Chem       Date:  2019-09-10       Impact factor: 4.354

Review 4.  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

5.  Cu-Catalyzed aromatic C-H imidation with N-fluorobenzenesulfonimide: mechanistic details and predictive models.

Authors:  Brandon E Haines; Takahiro Kawakami; Keiko Kuwata; Kei Murakami; Kenichiro Itami; Djamaladdin G Musaev
Journal:  Chem Sci       Date:  2016-10-19       Impact factor: 9.825

6.  Intermolecular Aryl C-H Amination through Sequential Iron and Copper Catalysis.

Authors:  Mohamed A B Mostafa; Ewen D D Calder; Daugirdas T Racys; Andrew Sutherland
Journal:  Chemistry       Date:  2016-12-16       Impact factor: 5.236

7.  Accelerated Ru-Cu Trinuclear Cooperative C-H Bond Functionalization of Carbazoles: A Kinetic and Computational Investigation.

Authors:  Alexander W Jones; Christian K Rank; Yanik Becker; Christian Malchau; Ignacio Funes-Ardoiz; Feliu Maseras; Frederic W Patureau
Journal:  Chemistry       Date:  2018-09-11       Impact factor: 5.236

8.  Radical-mediated direct C-H amination of arenes with secondary amines.

Authors:  Sebastian C Cosgrove; John M C Plane; Stephen P Marsden
Journal:  Chem Sci       Date:  2018-07-11       Impact factor: 9.825

9.  Electrooxidative para-selective C-H/N-H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives.

Authors:  Kun Liu; Shan Tang; Ting Wu; Shengchun Wang; Minzhu Zou; Hengjiang Cong; Aiwen Lei
Journal:  Nat Commun       Date:  2019-02-07       Impact factor: 14.919

10.  Design and Exploration of Catalytic Activity of Two-Dimensional Surface-Engineered Graphene Oxide Nanosheets in the Transannulation of N-Heterocyclic Aldehydes or Ketones with Alkylamines.

Authors:  Rakesh K Sharma; Aditi Sharma; Shivani Sharma; Sriparna Dutta; Sneha Yadav; Bhavya Arora
Journal:  ACS Omega       Date:  2019-02-12
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