Literature DB >> 24180555

Electrophilic difluoro(phenylthio)methylation: generation, stability, and reactivity of α-fluorocarbocations.

Nolan M Betterley1, Panida Surawatanawong, Samran Prabpai, Palangpon Kongsaeree, Chutima Kuhakarn, Manat Pohmakotr, Vichai Reutrakul.   

Abstract

Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of α-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2(+)).

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Year:  2013        PMID: 24180555     DOI: 10.1021/ol402631t

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


  2 in total

1.  Base Catalysis Enables Access to α,α-Difluoroalkylthioethers.

Authors:  Douglas L Orsi; Brandon J Easley; Ashley M Lick; Ryan A Altman
Journal:  Org Lett       Date:  2017-03-23       Impact factor: 6.005

2.  Acid-Catalyzed Hydrothiolation of gem-Difluorostyrenes to Access α,α-Difluoroalkylthioethers.

Authors:  Jacob P Sorrentino; Douglas L Orsi; Ryan A Altman
Journal:  J Org Chem       Date:  2021-01-20       Impact factor: 4.354

  2 in total

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