Literature DB >> 27271773

Mild and Low-Pressure fac-Ir(ppy)3 -Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis.

Shiao Y Chow1, Marc Y Stevens1, Linda Åkerbladh1, Sara Bergman1, Luke R Odell2.   

Abstract

A novel, mild and facile preparation of alkyl amides from unactivated alkyl iodides employing a fac-Ir(ppy)3 -catalyzed radical aminocarbonylation protocol has been developed. Using a two-chambered system, alkyl iodides, fac-Ir(ppy)3 , amines, reductants, and CO gas (released ex situ from Mo(CO)6 ), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a wide range of alkyl amides in moderate to excellent yields.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amides; carbonylation; photocatalysis; radical reactions

Year:  2016        PMID: 27271773     DOI: 10.1002/chem.201601694

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


  4 in total

1.  Cobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides.

Authors:  Brendon T Sargent; Erik J Alexanian
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-05       Impact factor: 15.336

2.  Visible-light-mediated Minisci C-H alkylation of heteroarenes with unactivated alkyl halides using O2 as an oxidant.

Authors:  Jianyang Dong; Xueli Lyu; Zhen Wang; Xiaochen Wang; Hongjian Song; Yuxiu Liu; Qingmin Wang
Journal:  Chem Sci       Date:  2018-11-27       Impact factor: 9.969

3.  Visible-Light-Enabled Aminocarbonylation of Unactivated Alkyl Iodides with Stoichiometric Carbon Monoxide for Application on Late-Stage Carbon Isotope Labeling.

Authors:  Malvika Sardana; Joakim Bergman; Cecilia Ericsson; Lee P Kingston; Magnus Schou; Christophe Dugave; Davide Audisio; Charles S Elmore
Journal:  J Org Chem       Date:  2019-12-11       Impact factor: 4.354

Review 4.  Recent Advances in Visible-Light-Mediated Amide Synthesis.

Authors:  Bin Lu; Wen-Jing Xiao; Jia-Rong Chen
Journal:  Molecules       Date:  2022-01-14       Impact factor: 4.411

  4 in total

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