1380071-02-2Relevant academic research and scientific papers
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
, p. 10626 - 10631 (2021)
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.
Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate, a difluorocarbene reagent with reactivity comparable to that of trimethylsilyl 2,2-difluoro-2- (fluorosulfonyl)acetate (TFDA)
Eusterwiemann, Steffen,Martinez, Henry,Dolbier, William R.
experimental part, p. 5461 - 5464 (2012/08/07)
Under specific high concentration, high temperature conditions, methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) has been found to act as a very efficient source of difluorocarbene, exhibiting carbene reactivity characteristics comparable to those exhibited by trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA). For example, in reaction with highly unreactive n-butyl acrylate and using only 2 equiv of MDFA, a yield of 76% of difluorocyclopropane product was obtained after 2 days.
