Literature DB >> 35782790

Advancements in Visible-Light-Enabled Radical C(sp)2-H Alkylation of (Hetero)arenes.

Alexandra C Sun1, Rory C McAtee1, Edward J McClain1, Corey R J Stephenson1.   

Abstract

The Minisci reaction, which encompasses the radical C-H alkylation of heteroarenes, has undergone revolutionary development in recent years. The application of photoredox catalysis for alkyl radical generation has given rise to a multitude of methods that feature enhanced functional group tolerance, generality, and operational simplicity. The intent of this short review is to bring readers up to date on this rapidly expanding field. Specifically, we will highlight key examples of visible light-driven Minisci alkylation strategies that represent key advancements in this area of research. The scope and limitation of these transformations will be discussed, with a focus on examining the underlying pathways for alkyl radical generation. Our goal is to make this short review a stepping stone for further synthetic research development.

Entities:  

Keywords:  Minisci reaction; heteroarenes; late-stage functionalization; photoredox catalysis; radical alkylation; visible light

Year:  2019        PMID: 35782790      PMCID: PMC9245688          DOI: 10.1055/s-0037-1611658

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   2.969


  52 in total

1.  Oxidation of alkyl trifluoroborates: an opportunity for tin-free radical chemistry.

Authors:  Geoffroy Sorin; Rocio Martinez Mallorquin; Yohan Contie; Alexandre Baralle; Max Malacria; Jean-Philippe Goddard; Louis Fensterbank
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

2.  Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles.

Authors:  Alexandra C Sun; Edward J McClain; Joel W Beatty; Corey R J Stephenson
Journal:  Org Lett       Date:  2018-06-01       Impact factor: 6.005

3.  Catalytic enantioselective Minisci-type addition to heteroarenes.

Authors:  Rupert S J Proctor; Holly J Davis; Robert J Phipps
Journal:  Science       Date:  2018-04-05       Impact factor: 47.728

Review 4.  Modern advances in heterocyclic chemistry in drug discovery.

Authors:  Alexandria P Taylor; Ralph P Robinson; Yvette M Fobian; David C Blakemore; Lyn H Jones; Olugbeminiyi Fadeyi
Journal:  Org Biomol Chem       Date:  2016-07-12       Impact factor: 3.876

5.  Visible light-mediated intermolecular C-H functionalization of electron-rich heterocycles with malonates.

Authors:  Laura Furst; Bryan S Matsuura; Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

Review 6.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

7.  Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling.

Authors:  Patricia Zhang; Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-06-22       Impact factor: 15.419

8.  Metal-free C-H alkylation of heteroarenes with alkyltrifluoroborates: a general protocol for 1°, 2° and 3° alkylation.

Authors:  Jennifer K Matsui; David N Primer; Gary A Molander
Journal:  Chem Sci       Date:  2017-03-06       Impact factor: 9.825

9.  Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine.

Authors:  Guo-Xing Li; Christian A Morales-Rivera; Yaxin Wang; Fang Gao; Gang He; Peng Liu; Gong Chen
Journal:  Chem Sci       Date:  2016-07-12       Impact factor: 9.825

10.  Discovery and mechanistic study of a photocatalytic indoline dehydrogenation for the synthesis of elbasvir.

Authors:  Hatice G Yayla; Feng Peng; Ian K Mangion; Mark McLaughlin; Louis-Charles Campeau; Ian W Davies; Daniel A DiRocco; Robert R Knowles
Journal:  Chem Sci       Date:  2015-12-07       Impact factor: 9.825

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  1 in total

1.  Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols.

Authors:  Avene C Colgan; Rupert S J Proctor; David C Gibson; Padon Chuentragool; Antti S K Lahdenperä; Kristaps Ermanis; Robert J Phipps
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-27       Impact factor: 16.823

  1 in total

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