Literature DB >> 28965407

Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light.

Peng Liu1,2, Wenbo Liu1, Chao-Jun Li1.   

Abstract

The Minisci alkylation is useful to functionalize aromatics via alkyl radical addition. Current approaches to prepare alkyl radicals follow either oxidative or reductive pathways from various functional groups. Developing new strategy beyond these traditional methods remains elusive yet highly significant. In this article, we present a redox-neutral and catalyst-free protocol to engender alkyl radicals in the context of trifluoromethylation and general alkylation of arenes. This protocol, via the Norrish type I concept to produce alkyl radicals, accommodates various functional groups and delivers the product in good yields. This method identified a series of compounds as the trifluoromethylation and alkylation reagents assisted by light. It is expected that these compounds can find potential applications in other radical-involved reactions.

Year:  2017        PMID: 28965407     DOI: 10.1021/jacs.7b08685

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  11 in total

1.  Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics.

Authors:  Durbis J Castillo-Pazos; Juan D Lasso; Chao-Jun Li
Journal:  Beilstein J Org Chem       Date:  2022-07-04       Impact factor: 2.544

2.  Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex.

Authors:  Pan Pan; Shihan Liu; Yu Lan; Huiying Zeng; Chao-Jun Li
Journal:  Chem Sci       Date:  2022-05-23       Impact factor: 9.969

3.  Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.

Authors:  Shuo Guo; Deyaa I AbuSalim; Silas P Cook
Journal:  J Am Chem Soc       Date:  2018-09-24       Impact factor: 15.419

4.  Cu and Hydroquinone for the Trifluoromethylation of Unprotected Phenols.

Authors:  Jakob Pletz; Christoph Koeberl; Michael Fuchs; Oliver Steiner; Walter Goessler; Wolfgang Kroutil
Journal:  European J Org Chem       Date:  2018-10-08

5.  Diacetyl as a "traceless" visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions.

Authors:  Chia-Yu Huang; Jianbin Li; Wenbo Liu; Chao-Jun Li
Journal:  Chem Sci       Date:  2019-04-08       Impact factor: 9.825

6.  Visible-light-induced transition metal and photosensitizer free decarbonylative addition of amino-arylaldehydes to ketones.

Authors:  Yi Wang; Yatao Lang; Chao-Jun Li; Huiying Zeng
Journal:  Chem Sci       Date:  2021-12-21       Impact factor: 9.825

7.  A cross-dehydrogenative C(sp3)-H heteroarylation via photo-induced catalytic chlorine radical generation.

Authors:  Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal:  Nat Commun       Date:  2021-06-29       Impact factor: 14.919

8.  Radical difluoromethylthiolation of aromatics enabled by visible light.

Authors:  Jianbin Li; Dianhu Zhu; Leiyang Lv; Chao-Jun Li
Journal:  Chem Sci       Date:  2018-06-01       Impact factor: 9.825

Review 9.  Recent Advances in Rapid Synthesis of Non-proteinogenic Amino Acids from Proteinogenic Amino Acids Derivatives via Direct Photo-Mediated C-H Functionalization.

Authors:  Zhenbo Yuan; Xuanzhong Liu; Changmei Liu; Yan Zhang; Yijian Rao
Journal:  Molecules       Date:  2020-11-12       Impact factor: 4.411

10.  Visible-Light Driven Selective C-N Bond Scission in anti-Bimane-Like Derivatives.

Authors:  Nejc Petek; Helena Brodnik; Uroš Grošelj; Jurij Svete; Franc Požgan; Bogdan Štefane
Journal:  Org Lett       Date:  2021-06-02       Impact factor: 6.005

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.