State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, 730000, Lanzhou, Gansu, China.
Department of Chemistry, University of South Florida, Tampa, 33620, FL, USA.
Nat Commun. 2018 May 17;9(1):1972. doi: 10.1038/s41467-018-04331-4.
Transition-metal-catalyzed diazo activation is a classical way to generate metal carbene, which are valuable intermediates in synthetic organic chemistry. An alternative iodine-catalyzed diazo activation is disclosed herein under either photo-initiated or thermal-initiated conditions, which represents an approach to enable carbene radical reactivity. This metal-free diazo activation strategy were successfully applied into olefin cyclopropanation and epoxidation, and applying this method to pyrrole synthesis under thermal-initiated conditions further demonstrates the unique reactivity using this method over typical metal-catalyzed conditions.
过渡金属催化的重氮活化是生成金属卡宾的经典方法，金属卡宾是合成有机化学中的重要中间体。本文揭示了一种在光引发或热引发条件下，碘催化的重氮活化方法，这代表了一种实现卡宾自由基反应性的方法。这种无金属的重氮活化策略已成功应用于烯烃环丙烷化和环氧化反应，并在热引发条件下将该方法应用于吡咯合成，进一步证明了与典型金属催化条件相比，该方法具有独特的反应性。
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