Literature DB >> 23930944

Stereoselective radical azidooxygenation of alkenes.

Bo Zhang1, Armido Studer.   

Abstract

Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.

Entities:  

Year:  2013        PMID： 23930944     DOI： 10.1021/ol402106x

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


  18 in total

1.  Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.

Authors:  Juno C Siu; Joseph B Parry; Song Lin
Journal:  J Am Chem Soc       Date:  2019-01-28       Impact factor: 15.419

2.  Practical Synthetic Procedures for the Iron-Catalyzed Intermolecular Olefin Aminohydroxylation Using Functionalized Hydroxylamines.

Authors:  Cheng-Liang Zhu; Deng-Fu Lu; Jeffrey D Sears; Zhen-Xin Jia; Hao Xu
Journal:  Synthesis (Stuttg)       Date:  2016-07-25       Impact factor: 3.157

3.  Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  J Org Chem       Date:  2019-01-17       Impact factor: 4.354

4.  Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.

Authors:  Kun Shen; Qiu Wang
Journal:  J Am Chem Soc       Date:  2017-09-05       Impact factor: 15.419

5.  Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

Authors:  Hongze Li; Shou-Jie Shen; Cheng-Liang Zhu; Hao Xu
Journal:  J Am Chem Soc       Date:  2019-05-30       Impact factor: 15.419

6.  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

7.  Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp3)-H Bonds with Zhdankin's λ3-Azidoiodane.

Authors:  Craig S Day; Alexander Fawcett; Ruchira Chatterjee; John F Hartwig
Journal:  J Am Chem Soc       Date:  2021-09-24       Impact factor: 16.383

8.  Electrochemical Azidooxygenation of Alkenes Mediated by a TEMPO-N3 Charge-Transfer Complex.

Authors:  Juno C Siu; Gregory S Sauer; Ambarneil Saha; Reed L Macey; Niankai Fu; Timothée Chauviré; Kyle M Lancaster; Song Lin
Journal:  J Am Chem Soc       Date:  2018-09-12       Impact factor: 15.419

9.  Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners.

Authors:  Minyan Li; Simon Berritt; Lucas Matuszewski; Guogang Deng; Ana Pascual-Escudero; Grace B Panetti; Michal Poznik; Xiaodong Yang; Jason J Chruma; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2017-10-31       Impact factor: 15.419

10.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419
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