光氧化还原催化的1,2,3-苯并三嗪-4(3H)-酮与末端烯烃的串联脱氮[4 + 2]环化反应
Photoredox Catalyzed Tandem Denitrogenative [4 + 2] Annulation of 1,2,3-Benzotriazin-4(3H)-ones with Terminal Olefins.
作者信息
Li Haiqiong, Zhang Yu, Han Fen, Zhang Zhengbing, Yin Mengyun, Han Pan, Jing Linhai
机构信息
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P. R. China.
Panzhihua No. 3 Senior High School, Panzhihua 617000, P. R. China.
出版信息
J Org Chem. 2024 Nov 1;89(21):16043-16048. doi: 10.1021/acs.joc.4c02043. Epub 2024 Oct 14.
The dihydroisoquinolones skeleton is ubiquitous in natural products and biological molecules. Reported strategies for constructing dihydroisoquinolones usually require noble metal catalysts or stoichiometric oxidants, which limit their wide applications. Herein, we developed a photoredox catalyzed tandem denitrogenative [4 + 2] annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with terminal olefins. A variety of dihydroisoquinolones can be accessed in moderate to excellent yield. This protocol features high atom-economy, mild reaction conditions, and is external oxidant-free, enabling the synthesis of various substituted dihydroisoquinolones.
二氢异喹啉酮骨架广泛存在于天然产物和生物分子中。报道的构建二氢异喹啉酮的策略通常需要贵金属催化剂或化学计量的氧化剂，这限制了它们的广泛应用。在此，我们开发了一种光氧化还原催化的1,2,3-苯并三嗪-4(3H)-酮与末端烯烃的串联脱氮[4 + 2]环化反应。可以以中等至优异的产率获得各种二氢异喹啉酮。该方法具有高原子经济性、温和的反应条件且无需外部氧化剂，能够合成各种取代的二氢异喹啉酮。
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