Jiang Min, Yang Haijun, Lefebvre Quentin, Su Jihu, Fu Hua
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China.
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
iScience. 2018 Aug 31;6:102-113. doi: 10.1016/j.isci.2018.07.011. Epub 2018 Jul 20.
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.
碳 - 碳双键（C=C）的形成是有机化学中的关键转化反应。可见光光氧化还原催化为新型独特有机反应的开发提供了经济且可持续的机遇。在此，我们报道了一种以三苯基膦作为还原猝灭剂，通过可见光光氧化还原催化实现卤代烃与醛进行烯烃化反应的方法（103个实例）。该转化反应适用于多种醛，包括多聚甲醛、甲醛水溶液、2,2,2 - 三氟乙醛一水合物、2,2,2 - 三氟 - 1 - 甲氧基乙醇以及其他常见醛类。本方法具有若干优点，包括操作简便、反应条件温和、官能团耐受性广以及适用于克级规模合成。我们预计它将广泛应用于有机分子、天然产物、生物分子及聚合物的合成。
