Literature DB >> 33261315

Trisulfur-Radical-Anion-Triggered C(sp2)-H Amination of Electron-Deficient Alkenes.

Khang X Nguyen1,2, Phuc H Pham1,2, Thao T Nguyen1,2,3, Chou-Hsun Yang4, Hoai T B Pham1,2,4, Tung T Nguyen1,2, Haobin Wang4, Nam T S Phan1,2.   

Abstract

A trisulfur-radical-anion (S3̇-)-triggered C(sp2)-H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations suggest that S3̇- initiates the nucleophilic attacks via a thiirane intermediate.

Entities:  

Year:  2020        PMID: 33261315     DOI: 10.1021/acs.orglett.0c03846

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


  1 in total

1.  Late-Stage Amination of Drug-Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium-Catalyzed C-H Activation.

Authors:  Erik Weis; Magnus J Johansson; Belén Martín-Matute
Journal:  Chemistry       Date:  2021-11-17       Impact factor: 5.020

  1 in total

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