Palladium-Catalyzed Cascade Arylation of Vinylogous Esters Enabled by Tris(1-adamantyl)phosphine
- Yi-Chi YangYi-Chi YangDepartment of Applied Chemistry, National Chiao Tung University, 1001 University Road, Hsinchu 30010, TaiwanMore by Yi-Chi Yang
- Yi-Ching LinYi-Ching LinDepartment of Applied Chemistry, National Chiao Tung University, 1001 University Road, Hsinchu 30010, TaiwanMore by Yi-Ching Lin
- , and
- Yen-Ku Wu*
Described is a method for the transformation of a cyclic vinylogous ester to the corresponding polyarylated product. We found a catalytic system comprising palladium diacetate and tris(1-adamantyl)phosphine is quite effective in promoting a set of controlled cascade arylations. As a result, a range of novel (hetero)aryl-containing scaffolds was synthesized with a high level of efficiency.
This article is cited by 9 publications.
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- Mei Wang, Wei Wang, Dashan Li, Wen-Jing Wang, Rui Zhan, Li-Dong Shao. α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds. Natural Products and Bioprospecting 2021, 11 (4) , 379-404. https://doi.org/10.1007/s13659-021-00312-1
- Yi‐Kang Song, Si‐Yu Xu, Shu‐Sheng Zhang, Jian‐Guo Fu, Guo‐Qiang Lin, Chen‐Guo Feng. Palladium‐Catalyzed Tandem γ‐Arylation/Aromatization of Cyclohex‐2‐En‐1‐One Derivatives: A Route to 3,4‐Dihydroanthracen‐1(2 H )‐Ones. Advanced Synthesis & Catalysis 2021, 363 (12) , 3001-3005. https://doi.org/10.1002/adsc.202001587
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