Literature DB >> 27116936

New amination strategies based on nitrogen-centered radical chemistry.

Tao Xiong1, Qian Zhang.   

Abstract

The interesting and diverse biological activities of nitrogen-containing compounds make the construction of the C-N bond of great importance. Despite the tremendous advances that have been made in this research field, C-N bond formation based on n class="Chemical">nitrogen-centered radicals remains a significant challenge due to the harsh conditions required for the generation of nitrogen-centered radicals and their propensity for hydrogen abstraction or engaging in other degradation pathways. In the past several years, novel methodologies for C-N bond constructions based on nitrogen centered-radical intermediates, coordinated with metal or generated in the presence of visible-light and a photocatalyst, have attracted considerable attention. This tutorial review will summarize the significant progress of these efficient and mild radical amination reactions, with an emphasis on approaches for the generation of nitrogen-centered radicals and their reaction patterns, related mechanisms and synthetic applications, as well as unmet challenges in this emerging and promising field.

Entities:  

Year:  2016        PMID: 27116936     DOI: 10.1039/c5cs00852b

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  51 in total

1.  Direct Access to Versatile Electrophiles via Catalytic Oxidative Cyanation of Alkenes.

Authors:  De-Wei Gao; Ekaterina V Vinogradova; Sri Krishna Nimmagadda; Jose M Medina; Yiyang Xiao; Radu M Suciu; Benjamin F Cravatt; Keary M Engle
Journal:  J Am Chem Soc       Date:  2018-06-22       Impact factor: 15.419

2.  Exploiting Imine Photochemistry for Masked N-Centered Radical Reactivity.

Authors:  Daryl Staveness; James L Collins; Rory C McAtee; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-08       Impact factor: 15.336

3.  Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.

Authors:  Sherry R Chemler; Shuklendu D Karyakarte; Zainab M Khoder
Journal:  J Org Chem       Date:  2017-09-29       Impact factor: 4.354

4.  Asymmetric Induction and Enantiodivergence in Catalytic Radical C-H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution.

Authors:  Kai Lang; Sebastian Torker; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2019-07-29       Impact factor: 15.419

5.  Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes.

Authors:  Suraj K Ayer; J L Roizen
Journal:  J Org Chem       Date:  2019-02-26       Impact factor: 4.354

6.  Enantioselective Intermolecular Radical C-H Amination.

Authors:  Li-Mei Jin; Pan Xu; Jingjing Xie; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2020-11-25       Impact factor: 15.419

7.  Catalytic Alkene Difunctionalization via Imidate Radicals.

Authors:  Kohki M Nakafuku; Stacy C Fosu; David A Nagib
Journal:  J Am Chem Soc       Date:  2018-08-29       Impact factor: 15.419

8.  Mechanism of Photoredox-Initiated C-C and C-N Bond Formation by Arylation of IPrAu(I)-CF3 and IPrAu(I)-Succinimide.

Authors:  Suhong Kim; F Dean Toste
Journal:  J Am Chem Soc       Date:  2019-01-17       Impact factor: 15.419

9.  Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds.

Authors:  Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-07       Impact factor: 15.336

10.  C-N Cross-Coupling via Photoexcitation of Nickel-Amine Complexes.

Authors:  Chern-Hooi Lim; Max Kudisch; Bin Liu; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2018-06-11       Impact factor: 15.419

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