Literature DB >> 29326995

Alkene functionalization for the stereospecific synthesis of substituted aziridines by visible-light photoredox catalysis.

Wan-Lei Yu1, Jian-Qiang Chen, Yun-Long Wei, Zhu-Yin Wang, Peng-Fei Xu.   

Abstract

A novel strategy involving visible-light-induced functionalization of alkenes for the synthesis of substituted aziridines was developed. The readily prepared N-protected 1-aminopyridinium salts were used for the generation of N-centered radicals. This approach allowed the synthesis of aziridines bearing various functional groups with excellent diastereoselectivity under mild conditions. Moreover, this protocol was successfully applied to prepare structurally diverse nitrogen-containing frameworks.

Entities:  

Year:  2018        PMID: 29326995     DOI: 10.1039/c7cc09151f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  8 in total

1.  Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.

Authors:  Logan A Combee; Shea L Johnson; Julie E Laudenschlager; Michael K Hilinski
Journal:  Org Lett       Date:  2019-03-25       Impact factor: 6.005

Review 2.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

3.  Diversification of Amidyl Radical Intermediates Derived from C-H Aminopyridylation.

Authors:  Asim Maity; Pritam Roychowdhury; Roberto G Herrera; David C Powers
Journal:  Org Lett       Date:  2022-04-04       Impact factor: 6.072

4.  N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines.

Authors:  Hao Tan; Samya Samanta; Asim Maity; Pritam Roychowdhury; David C Powers
Journal:  Nat Commun       Date:  2022-06-10       Impact factor: 17.694

5.  Theoretical investigation of the regioselective ring opening of 2-methylaziridine. Lewis acid effect.

Authors:  Emna Cherni; Khaled Essalah; Néji Besbes; Manef Abderrabba; Sameh Ayadi
Journal:  J Mol Model       Date:  2018-10-09       Impact factor: 1.810

6.  Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents.

Authors:  Yonghoon Moon; Bohyun Park; Inwon Kim; Gyumin Kang; Sanghoon Shin; Dahye Kang; Mu-Hyun Baik; Sungwoo Hong
Journal:  Nat Commun       Date:  2019-09-11       Impact factor: 14.919

7.  Metal-free, visible-light induced enantioselective three-component dicarbofunctionalization and oxytrifluoromethylation of enamines via chiral phosphoric acid catalysis.

Authors:  Hui Liang; Dong-Sheng Ji; Guo-Qiang Xu; Yong-Chun Luo; Haixue Zheng; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-01-04       Impact factor: 9.825

8.  Visible Light-Mediated Direct C-H Aroylation and Alkylation of Heteroarenes.

Authors:  Rui Chang; Jie Fang; Jian-Qiang Chen; Dan Liu; Guo-Qiang Xu; Peng-Fei Xu
Journal:  ACS Omega       Date:  2019-08-14
  8 in total

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