Literature DB >> 23578034

Iron-catalyzed oxidative C(3)-H functionalization of amines.

Noriaki Takasu1, Kounosuke Oisaki, Motomu Kanai.   

Abstract

Fe-catalyzed direct dehydrogenative C(3)-functionalization of tertiary arylamines was developed via activation of the sp(3) C(3)-H bond. The reaction is applicable to both cyclic and acyclic amines. The key process is the catalytic desaturative enamine formation from tertiary amines and position-selective C-C bond formation (addition to nitro olefins) at the β-carbon. Products can be converted to versatile and unique nitrogen-containing molecules.

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Year:  2013        PMID: 23578034     DOI: 10.1021/ol400568u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Authors:  Longle Ma; Anirudra Paul; Martin Breugst; Daniel Seidel
Journal:  Chemistry       Date:  2016-11-09       Impact factor: 5.236

2.  β-Functionalization of Saturated Aza-Heterocycles Enabled by Organic Photoredox Catalysis.

Authors:  Natalie Holmberg-Douglas; Younggi Choi; Brian Aquila; Hoan Huynh; David A Nicewicz
Journal:  ACS Catal       Date:  2021-02-24       Impact factor: 13.700

3.  Redox-neutral α,β-difunctionalization of cyclic amines.

Authors:  Weijie Chen; YoungKu Kang; Richard G Wilde; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336

4.  N-Heterocyclic Carbene Ligand-Enabled C(sp(3))-H Arylation of Piperidine and Tetrahydropyran Derivatives.

Authors:  Shengqing Ye; Weibo Yang; Timothy Coon; Dewey Fanning; Tim Neubert; Dean Stamos; Jin-Quan Yu
Journal:  Chemistry       Date:  2016-02-24       Impact factor: 5.236

5.  Rapid functionalization of multiple C-H bonds in unprotected alicyclic amines.

Authors:  Weijie Chen; Anirudra Paul; Khalil A Abboud; Daniel Seidel
Journal:  Nat Chem       Date:  2020-03-30       Impact factor: 24.427

6.  Direct access to functionalized azepanes by cross-coupling with α-halo eneformamides.

Authors:  Timothy K Beng; Sidney M Wilkerson-Hill; Richmond Sarpong
Journal:  Org Lett       Date:  2014-01-23       Impact factor: 6.005

7.  Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.

Authors:  Alexander J Grenning; John K Snyder; John A Porco
Journal:  Org Lett       Date:  2014-01-10       Impact factor: 6.005

8.  Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids.

Authors:  Hannah M S Haley; Stefan E Payer; Sven M Papidocha; Simon Clemens; Jonathan Nyenhuis; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2021-03-17       Impact factor: 16.383

9.  Oxidative β-C-H sulfonylation of cyclic amines.

Authors:  R J Griffiths; W C Kong; S A Richards; G A Burley; M C Willis; E P A Talbot
Journal:  Chem Sci       Date:  2018-01-22       Impact factor: 9.825

  9 in total

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