342-23-4Relevant articles and documents
Pd-Catalysed direct C(sp2)-H fluorination of aromatic ketones: Concise access to anacetrapib
Wu, Qiuzi,Mao, Yang-Jie,Zhou, Kun,Wang, Shuang,Chen, Lei,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian
, p. 4544 - 4547 (2021/05/17)
The Pd-cataylsed direct ortho-C(sp2)-H fluorination of aromatic ketones has been developed for the first time. The reaction features good regioselectivity and simple operations, constituting an alternative shortcut to access fluorinated ketones. A concise synthesis of anacetrapib has also been achieved by using late-stage C-H fluorination as a key step.
Tailoring Diindenochrysene through Intramolecular Multi-Assemblies by C?F Bond Activation on Aluminum Oxide
Akhmetov, Vladimir,Feofanov, Mikhail,Troyanov, Sergey,Amsharov, Konstantin
, p. 7607 - 7612 (2019/05/15)
The unique nature of the alumina-mediated cyclodehydrofluorination gives the opportunity to execute the preprogrammed algorithm of the C?C couplings rationally built into a precursor. Such multi-assemblies facilitate the construction of the carbon-skeleton, superseding the conventional step-by-step by the one-pot intramolecular assembly. In this work, the feasibility of the alumina-mediated C?F bond activation approach for multi-assembly is demonstrated on the example of a fundamental bowl-shaped polycyclic aromatic hydrocarbon (diindenochrysene) through the formation of all “missing” C?C bonds at the last step. Beside valuable insights into the reaction mechanism and the design of the precursors, a facile pathway enabling the two-step synthesis of diindenochrysene was elaborated, in which five C?C bonds form in a single synthetic step. It is shown that the relative positions of fluorine atoms play a crucial role in the outcome of the assembly and that governing the substituent positions enables the design of effective precursor molecules “programmed” for the consecutive C?C bond formations. In general, these findings push the state of the field towards the facile synthesis of sophisticated bowl-shaped carbon-based nanostructures through multi-assembly of fluoroarenes.
Ligand-Free Palladium-Catalyzed Oxidative Carbonylative Homocoupling of Arylboron Reagents at Ambient Pressure
Zhao, Hongyuan,Han, Wei
supporting information, p. 4279 - 4283 (2016/09/14)
Arylboronic acids or potassium aryltrifluoroborates were readily oxidatively carbonylated to their corresponding diaryl ketones in high yields with high selectivities by ligand-free palladium-catalyzed homocoupling at atmospheric pressure. This novel method employs molecular oxygen or iodine as the oxidant and offers an attractive alternative to transition-metal-based oxidant systems.