Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
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DOI：
10.1002/anie.201905485
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发表时间：
2019-08-27
影响因子：
16.6
通讯作者：
Koenig, Burkhard
中科院分区：
文献类型：
--
作者：
Chatterjee, Anamitra;Koenig, Burkhard
通过可见光照射直接还原芳烃和杂芳烃仍然具有挑战性，因为单个光子的能量不足以破坏芳香族稳定性。本文所示的是，两个可见光光子的能量积累允许芳烃和杂芳烃的脱芳构化。机理研究证实，能量转移和电子转移过程的组合产生的芳烃自由基阴离子，随后被捕获的氢原子转移，最后质子化，形成脱芳构化的产品。光还原将平面芳族原料化合物转化为可用于有机合成的分子骨架。
The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.