State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, People's Republic of China.
Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing 100048, People's Republic of China.
J Org Chem. 2021 Sep 17;86(18):12772-12782. doi: 10.1021/acs.joc.1c01363. Epub 2021 Aug 30.
Herein, we describe a convenient general protocol for monofluoroalkenylation reactions of alkyl bromides involving cooperative visible-light photoredox catalysis and halogen abstraction. Mechanistic experiments showed that the products were generated by selective cross-coupling of aliphatic radicals with fluoroalkenyl radicals. Silyl radical-mediated halogen abstraction enabled the protocol to be used for the monofluoroalkenylation of a broad range of alkyl and heteroaryl halides. The protocol could be carried out on a gram scale and was applied to cholesterol, indicating its utility for late-stage monofluoroalkenylation reactions.
在这里，我们描述了一种方便的烷基溴的单氟烯基化反应的通用协议，涉及协同可见光光氧化还原催化和卤化物的提取。 机理实验表明，产物是通过脂肪族自由基与氟烯基自由基的选择性交叉偶联生成的。 硅自由基介导的卤化物提取使该方案能够用于广泛的烷基和杂芳基卤化物的单氟烯基化。 该方案可以在克级规模下进行，并应用于胆固醇，表明其在后期单氟烯基化反应中的实用性。
