6967-88-0Relevant articles and documents
Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium
Romero, Kevin J.,Keylor, Mitchell H.,Griesser, Markus,Zhu, Xu,Strobel, Ethan J.,Pratt, Derek A.,Stephenson, Corey R.J.
, p. 6499 - 6504 (2020)
The first total synthesis of the resveratrol tetramers vitisin A and vitisin D is reported. Electrochemical generation and selective dimerization of persistent radicals is followed by thermal isomerization of the symmetric C8b-C8c dimer to the C3c-C8b isomer, providing rapid entry into the vitisin core. Computational results suggest that this synthetic approach mimics Nature's strategy for constructing these complex molecules. Sequential acid-mediated rearrangements consistent with the proposed biogenesis of these compounds afford vitisin A and vitisin D. The rapid synthesis of these complex molecules will enable further study of their pharmacological potential.
Visible light-induced mono-bromination of arenes with BrCCl3
Fan, Jiali,Wei, Qiancheng,Zhu, Ershu,Gao, Jing,Cheng, Xiamin,Lu, Yongna,Loh, Teck-Peng
supporting information, p. 5977 - 5980 (2021/06/18)
A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.
Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics
Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung
supporting information, p. 4448 - 4452 (2018/10/17)
Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.