4.6 Article

Access to α,α-difluoro(arylthio)methyl oxetanes from α,α-difluoro(arylthio)methyl ketones and trimethylsulfoxonium halides: scope, mechanism and applications

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 20, 期 7, 页码 1500-1509

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob02268g

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资金

  1. National Natural Science Foundation of China [21702064]
  2. Guangdong Basic and Applied Basic Research Foundation [2020B1515020012]
  3. National Undergraduate Innovative and Entrepreneurial Training Program [202110561030]

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A general and practical method for the synthesis of alpha,alpha-difluoro(arylthio)methyl oxetanes has been reported. This method involves the reaction of alpha,alpha-difluoro(arylthio)methyl ketones with trimethylsulfoxonium halides, and features mild conditions, operational simplicity, a broad substrate scope, and high yields.
A general and practical method for the synthesis of alpha,alpha-difluoro(arylthio)methyl oxetanes that occurs by the reaction of alpha,alpha-difluoro(arylthio)methyl ketones with trimethylsulfoxonium halides is reported. This reaction proceeds via the sequential Corey-Chaykovsky epoxidation and regioselective ring-expansion pathways and features mild conditions, operational simplicity, gram-scalability, a broad substrate scope and high yields. alpha,alpha-Difluoro(arylthio)methyl oxiranes have been shown to be the reaction intermediates. The obtained alpha,alpha-difluoro(arylthio)methyl oxetanes were further converted into useful sulfone, butenolide, and tetrahydrofuran derivatives.

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