54672-45-6Relevant academic research and scientific papers
Palladium-Catalyzed Ring-Opening Coupling of gem-Difluorocyclopropanes for the Construction of 2-Fluoroallylic Sulfones
Ni, Jiabin,Nishonov, Bekzod,Pardaev, Azizbek,Zhang, Ao
, p. 13646 - 13654 (2019)
A Pd-catalyzed ring-opening sulfonylation of gem-difluorocyclopropanes is reported. This protocol involves C-C bond cleavage, β-F elimination, and allylic coupling to form corresponding 2-fluoroallylic sulfones efficiently with Z-selectivity. Different substrates bearing diverse functional groups are tolerated. Moreover, this method is successfully used for the late-stage derivation of several bioactive molecules.
Rhodium Catalyzed Regioselective C?H Allylation of Simple Arenes via C?C Bond Activation of Gem-difluorinated Cyclopropanes
Jiang, Zhong-Tao,Huang, Jiangkun,Zeng, Yaxin,Hu, Fangdong,Xia, Ying
supporting information, p. 10626 - 10631 (2021/04/05)
Herein, we report a rhodium catalyzed directing-group free regioselective C?H allylation of simple arenes. Readily available gem-difluorinated cyclopropanes can be employed as highly reactive allyl surrogates via a sequence of C?C and C?F bond activation, providing allyl arene derivatives in good yields with high regioselectivity under mild conditions. The robust methodology enables facile late-stage functionalization of complex bioactive molecules. The high efficiency of this reaction is also demonstrated by the high turnover number (TON, up to 1700) of the rhodium catalyst on gram-scale experiments. Preliminary success on kinetic resolution of this transformation is achieved, providing a promising access to enantio-enriched gem-difluorinated cyclopropanes.
