Literature DB >> 26179746

Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis.

Kazuki Miyazawa1, Takashi Koike2, Munetaka Akita3.   

Abstract

A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N-protected 1-aminopyridinium salts are the key compounds and serve as amidyl radical precursors by the action of Ir photocatalysts, fac-[Ir(ppy)3] and [Ir(ppy)2 (dtbbpy)](PF6) (ppy=2-pyridylphenyl, dtbbpy=4,4'-di-tert-butyl-2,2'-bipyridine). The present photocatalytic system allows for synthesis of vicinal aminoalcohol derivatives from olefins with various functional groups under mild reaction conditions with easy handling.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; carbocations; electron transfer; homogeneous catalysis; photochemistry

Year:  2015        PMID: 26179746     DOI: 10.1002/chem.201501590

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


  10 in total

1.  Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Authors:  Honghui Lei; John H Conway; Caleb C Cook; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-07-16       Impact factor: 15.419

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.  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

6.  Bifunctional sulfilimines enable synthesis of multiple N-heterocycles from alkenes.

Authors:  Qiang Cheng; Zibo Bai; Srija Tewari; Tobias Ritter
Journal:  Nat Chem       Date:  2022-07-25       Impact factor: 24.274

7.  Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation.

Authors:  Xiao-Qiang Hu; Xiaotian Qi; Jia-Rong Chen; Quan-Qing Zhao; Qiang Wei; Yu Lan; Wen-Jing Xiao
Journal:  Nat Commun       Date:  2016-04-06       Impact factor: 14.919

8.  Photoredox Imino Functionalizations of Olefins.

Authors:  Jacob Davies; Nadeem S Sheikh; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-22       Impact factor: 15.336

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

10.  Enantioselective catalytic β-amination through proton-coupled electron transfer followed by stereocontrolled radical-radical coupling.

Authors:  Zijun Zhou; Yanjun Li; Bowen Han; Lei Gong; Eric Meggers
Journal:  Chem Sci       Date:  2017-06-15       Impact factor: 9.825

  10 in total

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