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Olefination of Alkyl Halides with Aldehydes by Merging Visible-Light Photoredox Catalysis and Organophosphorus Chemistry

Research output: Contribution to journalArticle

  • Min Jiang
  • Haijun Yang
  • Quentin Lefebvre
  • Jihu Su
  • Hua Fu
Original languageEnglish
Pages (from-to)102-113
Number of pages12
JournaliScience
Volume6
DOIs
DateAccepted/In press - 11 Jul 2018
DatePublished (current) - 31 Aug 2018

Abstract

Carbon-carbon double bond (C=C) formation is a crucial transformation in organic chemistry. Visible-light photoredox catalysis provides economical and sustainable opportunities for the development of novel and peculiar organic reactions. Here we report a method for the olefination of alkyl halides with aldehydes by visible-light photoredox catalysis using triphenylphosphine as a reductive quencher (103 examples). This transformation accommodates a variety of aldehydes including paraformaldehyde; aqueous formaldehyde; 2,2,2-trifluoroacetaldehyde monohydrate; 2,2,2-trifluoro-1-methoxyethanol; and other common aldehydes. The present method exhibits several advantages, including operational simplicity, mild reaction conditions, wide functional group tolerance, and amenability to gram-scale synthesis. We anticipate that it will be widely used in the synthesis of organic molecules, natural products, biological molecules, and polymers.

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    Rights statement: This is the final published version of the article (version of record). It first appeared online via Elsevier at https://doi.org/10.1016/j.isci.2018.07.011 . Please refer to any applicable terms of use of the publisher.

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