Blue-Light-Induced Carbene-Transfer Reactions of Diazoalkanes
Blue-Light-Induced Carbene-Transfer Reactions of Diazoalkanes
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DOI：
10.1002/anie.201811991
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发表时间：
2019-01-21
影响因子：
16.6
通讯作者：
Koenigs, Rene M.
中科院分区：
文献类型：
--
作者：
Hommelsheim, Rene;Guo, Yujing;Koenigs, Rene M.
卡宾是合成各种复杂分子的重要反应中间体，在有机合成和药物开发中有着广泛的应用。通常，它们的化学性质通过使用过渡金属催化剂来获得。在此，我们描述了应用低能量蓝光从给体-受体重氮烷光化学生成卡宾。这种无催化剂且操作简单的方法能够在温和的反应条件下实现与炔的高效环丙烯化反应和硫化物的重排，可用于间歇和连续流工艺。
Carbenes are very important reactive intermediates to access a variety of complex molecules and are applied widely in organic synthesis and drug discovery. Typically, their chemistry is accessed by the use of transition metal catalysts. Herein, we describe the application of low-energy blue light for the photochemical generation of carbenes from donor-acceptor diazoalkanes. This catalyst-free and operationally simple approach enables highly efficient cyclopropenation reactions with alkynes and the rearrangement of sulfides under mild reaction conditions, which can be utilized for both batch and continuous-flow processes.