Literature DB >> 28004917

Non-Deprotonative Primary and Secondary Amination of (Hetero)Arylmetals.

Zhe Zhou1, Zhiwei Ma1, Nicole Erin Behnke1, Hongyin Gao1, László Kürti1.   

Abstract

Herein we disclose a novel method for the facile transfer of primary (-NH2) and secondary amino groups (-n class="Chemical">NHR) to heteroaryl- as well as arylcuprates at low temperature without the need for precious metal catalysts, ligands, excess reagents, protecting and/or directing groups. This one-pot transformation allows unprecedented functional group tolerance and it is well-suited for the amination of electron-rich, electron-deficient as well as structurally complex (hetero)arylmetals. In some of the cases, only catalytic amounts of a copper(I) salt is required.

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Year:  2016        PMID: 28004917      PMCID: PMC5348115          DOI: 10.1021/jacs.6b12712

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


  17 in total

1.  General preparation of primary, secondary, and tertiary aryl amines by the oxidative coupling of polyfunctional aryl and heteroaryl amidocuprates.

Authors:  Vicente Del Amo; Srinivas Reddy Dubbaka; Arkady Krasovskiy; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

2.  Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2011       Impact factor: 9.825

Review 3.  Biaryl phosphane ligands in palladium-catalyzed amination.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 4.  Transition-Metal-Catalyzed Electrophilic Amination: Application of O-Benzoylhydroxylamines in the Construction of the C-N Bond.

Authors:  Xu Dong; Qing Liu; Yunhui Dong; Hui Liu
Journal:  Chemistry       Date:  2016-07-26       Impact factor: 5.236

5.  Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration.

Authors:  Noriyuki Tezuka; Kohei Shimojo; Keiichi Hirano; Shinsuke Komagawa; Kengo Yoshida; Chao Wang; Kazunori Miyamoto; Tatsuo Saito; Ryo Takita; Masanobu Uchiyama
Journal:  J Am Chem Soc       Date:  2016-07-14       Impact factor: 15.419

6.  Regio- and chemoselective multiple functionalization of chloropyrazine derivatives. Application to the synthesis of coelenterazine.

Authors:  Marc Mosrin; Tomke Bresser; Paul Knochel
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

7.  (tmp)(2)Zn x 2 MgCl(2) x 2 LiCl: a chemoselective base for the directed zincation of sensitive arenes and heteroarenes.

Authors:  Stefan H Wunderlich; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Copper-catalyzed electrophilic amination of diorganozinc reagents.

Authors:  Ashley M Berman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2004-05-12       Impact factor: 15.419

9.  N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Authors:  Zhihui Zhang; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-06-17       Impact factor: 6.005

10.  Advances in the chemistry of oxaziridines.

Authors:  Kevin S Williamson; David J Michaelis; Tehshik P Yoon
Journal:  Chem Rev       Date:  2014-04-22       Impact factor: 60.622

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  9 in total

1.  Direct and Stereospecific Synthesis of N-H and N-Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids.

Authors:  Zhiwei Ma; Zhe Zhou; László Kürti
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

2.  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

Review 3.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

4.  A Strategy to Aminate Pyridines, Diazines, and Pharmaceuticals via Heterocyclic Phosphonium Salts.

Authors:  Chirag Patel; Margaret Mohnike; Michael C Hilton; Andrew McNally
Journal:  Org Lett       Date:  2018-04-17       Impact factor: 6.005

5.  Chemoselective Primary Amination of Aryl Boronic Acids by PIII/PV═O-Catalysis: Synthetic Capture of the Transient Nef Intermediate HNO.

Authors:  Seung Youn Hong; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2022-05-12       Impact factor: 16.383

6.  Site-selective amination and/or nitrilation via metal-free C(sp2)-C(sp3) cleavage of benzylic and allylic alcohols.

Authors:  Raghunath Reddy Anugu; John R Falck
Journal:  Chem Sci       Date:  2022-04-05       Impact factor: 9.969

7.  Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates.

Authors:  Pritam Roychowdhury; Roberto G Herrera; Hao Tan; David C Powers
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-20       Impact factor: 16.823

8.  Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt.

Authors:  Logan A Combee; Balaram Raya; Daoyong Wang; Michael K Hilinski
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

9.  Synthesis of Arylamines via Aminium Radicals.

Authors:  Thomas D Svejstrup; Alessandro Ruffoni; Fabio Juliá; Valentin M Aubert; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-24       Impact factor: 15.336

  9 in total

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