Literature DB >> 27897346

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions.

Jianzhong Liu1, Kai Wu1, Tao Shen1, Yujie Liang1, Miancheng Zou1, Yuchao Zhu1, Xinwei Li1, Xinyao Li1, Ning Jiao1,2.   

Abstract

A novel and efficient Fe-catalyzed direct C-H amination (NH2 ) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H functionalization; amination; iron; new reagents; radical

Year:  2016        PMID： 27897346     DOI： 10.1002/chem.201605476

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  10 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.  An Aminative Rearrangement of O-(Arenesulfonyl)hydroxylamines: Facile Access to ortho-Sulfonyl Anilines.

Authors:  Charlotte Morrill; James E Gillespie; Robert J Phipps
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-07       Impact factor: 16.823

3.  Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones.

Authors:  Si-Hua Hou; Adriana Y Prichina; Mengxi Zhang; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-12       Impact factor: 15.336

4.  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

5.  Direct Cα-heteroarylation of structurally diverse ethers via a mild N-hydroxysuccinimide mediated cross-dehydrogenative coupling reaction.

Authors:  Shihui Liu; Aoxia Liu; Yongqiang Zhang; Wei Wang
Journal:  Chem Sci       Date:  2017-03-24       Impact factor: 9.825

6.  Iron-Mediated Electrophilic Amination of Organozinc Halides using Organic Azides.

Authors:  Simon Graßl; Johannes Singer; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-19       Impact factor: 15.336

7.  Hydroxylamine-mediated C-C amination via an aza-hock rearrangement.

Authors:  Tao Wang; Philipp M Stein; Hongwei Shi; Chao Hu; Matthias Rudolph; A Stephen K Hashmi
Journal:  Nat Commun       Date:  2021-12-02       Impact factor: 14.919

Review 8.  The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines.

Authors:  Valentina C M Gasser; Szabolcs Makai; Bill Morandi
Journal:  Chem Commun (Camb)       Date:  2022-09-08       Impact factor: 6.065

Review 9.  Electrophilic Aminating Agents in Total Synthesis.

Authors:  Lauren G O'Neil; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-06       Impact factor: 16.823

10.  Hydroxylamine-Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron-Catalyzed Preparation of Unprotected Sulfinamides from Thiols.

Authors:  Sayanti Chatterjee; Szabolcs Makai; Bill Morandi
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-10       Impact factor: 16.823
  10 in total

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