180624-85-5Relevant articles and documents
Activation of C-H Bonds through Oxidant-Free Photoredox Catalysis: Cross-Coupling Hydrogen-Evolution Transformation of Isochromans and β-Keto Esters
Xiang, Ming,Meng, Qing-Yuan,Li, Jia-Xin,Zheng, Yi-Wen,Ye, Chen,Li, Zhi-Jun,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 18080 - 18484 (2015)
The direct and controlled activation of a C(sp3)-H bond adjacent to an O atom is of particular synthetic value for the conventional derivatization of ethers or alcohols. In general, stoichiometric amounts of an oxidant are required to remove an
Merging Photoredox with Br?nsted Acid Catalysis: The Cross-Dehydrogenative C?O Coupling for sp3 C?H Bond Peroxidation
Xia, Qing,Wang, Qiang,Yan, Changcun,Dong, Jianyang,Song, Hongjian,Li, Ling,Liu, Yuxiu,Wang, Qingmin,Liu, Xiangming,Song, Haibin
supporting information, p. 10871 - 10877 (2017/08/18)
A photoredox and Br?nsted acid synergistically catalyzed cross-dehydrogenative C?O coupling reaction is developed in which isochroman peroxyacetals are formed through sp3 C?H bond peroxidation. The reported method is characterized by its extremely mild reaction conditions, excellent yields, and broad substrate scope. An oxocarbenium ion p-chlorobenzenesulfonate was speculated to be the reactive intermediate. The role of hemiacetals and oxygenated dimers on the effective stabilization of the oxocarbenium ion was investigated; the presence of acid appeared to establish equilibrium between hemiacetals and oxygenated dimers with the oxocarbenium ion pairs. The broad applicability of the method highlights the potential of the protocol for molecule synthesis.
