Lv Shuaipeng, Li Qiannan, Sang Ji-Wei, Zhang Yu, Wang Jinxin, Zhang Wei-Dong
Shanghai Frontiers Science Center for Chinese Medicine Chemical Biology, Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine No. 1200, Cailun Road Shanghai 201203 China
School of Pharmacy, Second Military Medical University Shanghai 200433 China
RSC Adv. 2023 Apr 17;13(18):11929-11937. doi: 10.1039/d3ra01037f.
A homogeneous photocatalytic recyclable system for the selective radical-radical cross-coupling of -substituted amines and indoles has been established. This system could conduct in water or acetonitrile, featuring the reuse of uranyl nitrate as the recyclable photocatalyst a simple extraction. With this mild strategy in hand, good to excellent yields of cross-coupling products could be achieved even under the irradiation of sunlight, including 26 natural product derivatives and 16 natural product inspired re-engineered compounds. A radical-radical cross-coupling mechanism was newly proposed based on experimental evidence and reported literature. This strategy has been also applied to a gram scale synthesis to demonstrate its practical utility.
已建立了一种用于α-取代胺与吲哚的选择性自由基-自由基交叉偶联的均相光催化可循环系统。该系统可在水或乙腈中进行,其特点是硝酸铀酰作为可循环光催化剂可重复使用,且萃取简单。有了这种温和的策略,即使在阳光照射下也能实现良好至优异产率的交叉偶联产物,包括26种天然产物衍生物和16种天然产物启发的重新设计化合物。基于实验证据和已报道的文献,新提出了一种自由基-自由基交叉偶联机制。该策略还已应用于克级规模的合成,以证明其实际应用价值。