光诱导的无过渡金属和外部光敏剂的分子内芳基重排C(Ar)-O键裂解。
Photoinduced transition-metal- and external-photosensitizer-free intramolecular aryl rearrangement C(Ar)-O bond cleavage.
作者信息
Dou Qian, Li Chao-Jun, Zeng Huiying
机构信息
The State Key Laboratory of Applied Organic Chemistry , College of Chemistry and Chemical Engineering , Lanzhou University , 222 Tianshui Road , Lanzhou , 730000 , P. R. China . Email:
Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis , McGill University , 801 Sherbrooke St. West , Montreal , Quebec H3A 0B8 , Canada.
出版信息
Chem Sci. 2020 May 26;11(22):5740-5744. doi: 10.1039/d0sc01585g. eCollection 2020 Jun 14.
The use of photochemical reactions that do not require expensive photocatalysts or transition metals is an environmentally friendly strategy for accomplishing a variety of structural transformations. Herein, we report a protocol for photoinduced transition-metal- and external-photocatalyst-free intramolecular heteroaryl/aryl rearrangement reactions of 2-heteroaryl/aryloxybenzaldehydes. The protocol was compatible with a variety of functionalities, including methyl, methoxy, cyano, ester, trifluoromethyl, halogen, and heteroaromatic rings. Control experiments suggested that the reaction proceeded a photoinduced intramolecular heteroaryl/aryl rearrangement process involving photoexcitation of the aldehyde carbonyl group, radical addition, C-C bond formation and C(Ar)-O bond cleavage.
使用不需要昂贵光催化剂或过渡金属的光化学反应是实现各种结构转化的一种环境友好策略。在此，我们报告了一种用于2-杂芳基/芳氧基苯甲醛的光诱导无过渡金属和外部光催化剂的分子内杂芳基/芳基重排反应的方法。该方法与多种官能团兼容，包括甲基、甲氧基、氰基、酯基、三氟甲基、卤素和杂芳环。对照实验表明，该反应通过光诱导的分子内杂芳基/芳基重排过程进行，该过程涉及醛羰基的光激发、自由基加成、C-C键形成和C(Ar)-O键断裂。
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