Literature DB >> 27411560

Selective Oxytrifluoromethylation of Allylamines with CO2.

Jian-Heng Ye1, Lei Song1, Wen-Jun Zhou1,2, Tao Ju1, Zhu-Bao Yin1, Si-Shun Yan1, Zhen Zhang1, Jing Li1, Da-Gang Yu3.   

Abstract

Reported is the first oxy-trifluoromethylation of allylamines with carbon dioxide (CO2 ) using copper catalysis, thus leading to important CF3 -containing 2-oxazolidones. It is also the first time CO2 , a nontoxic and easily available greenhouse gas, has been used to tune the difunctionalization of alkenes from amino- to oxy-trifluoromethylation. Of particular note, this multicomponent reaction is highly chemo-, regio-, and diastereoselective under redox-neutral and mild reaction conditions. Moreover, these reactions feature good functional-group tolerance, broad substrate scope, easy scalability and facile product diversification. The important products could also be formed with either spirocycles or two adjacent tetrasubstituted carbon centers.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbon dioxide; copper; fluorine; heterocycles; reaction mechanisms

Year:  2016        PMID: 27411560     DOI: 10.1002/anie.201603352

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

Review 1.  In situ tether formation from amines and alcohols enabling highly selective Tsuji-Trost allylation and olefin functionalization.

Authors:  Ugo Orcel; Jérôme Waser
Journal:  Chem Sci       Date:  2016-11-10       Impact factor: 9.825

2.  Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2.

Authors:  Si-Shun Yan; Lei Zhu; Jian-Heng Ye; Zhen Zhang; He Huang; Huiying Zeng; Chao-Jun Li; Yu Lan; Da-Gang Yu
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

3.  CO2-Assisted asymmetric hydrogenation of prochiral allylamines.

Authors:  Tamara M de Winter; Jaddie Ho; Christopher J Alridge; Philip G Jessop
Journal:  RSC Adv       Date:  2022-02-28       Impact factor: 3.361

4.  Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

Authors:  Sadhan Jana; Ajay Verma; Rahul Kadu; Sangit Kumar
Journal:  Chem Sci       Date:  2017-07-10       Impact factor: 9.825

  4 in total

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