603985-53-1Relevant academic research and scientific papers
Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH2CH2] → [CF2CHF] Isosterism
Daniliuc, Constantin G.,Gilmour, Ryan,Mück-Lichtenfeld, Christian,Neufeld, Jessica,Stünkel, Timo
, p. 13647 - 13651 (2021/05/07)
Saturated, fluorinated carbocycles are emerging as important modules for contemporary drug discovery. To expand the current portfolio, the synthesis of novel trifluorinated tetralins has been achieved. Fluorinated methyleneindanes serve as convenient precursors and undergo efficient difluorinative ring expansion with in situ generated p-TolIF2 (>20 examples, up to >95 %). A range of diverse substituents are tolerated under standard catalysis conditions and this is interrogated by Hammett analysis. X-ray analysis indicates a preference for the CH?F bond to occupy a pseudo-axial orientation, consistent with stabilising σC?H→σC?F* interactions. The replacement of the symmetric [CH2?CH2] motif by [CF2?CHF] removes the conformational degeneracy intrinsic to the parent tetralin scaffold leading to a predictable half-chair. The conformational behavior of this novel structural balance has been investigated by computational analysis and is consistent with stereoelectronic theory.
Synthesis of aryl allylic fluorides by direct electrophilic fluorination of alkenes
Luo, Hai-Qing,Loh, Teck-Peng
supporting information; experimental part, p. 1554 - 1556 (2009/06/21)
Aryl allylic fluorides were synthesized in 47-83% yields by using Selectfluor as the electrophilic reagent in DMF. The outcome of this reaction may be explained by electronic effects while the reactivity was controlled by the stabilization effect of the aryl group on the benzylic cationic intermediates.
Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles
Ishimaru, Takehisa,Shibata, Norio,Horikawa, Takao,Yasuda, Naomi,Nakamura, Shuichi,Toru, Takeshi,Shiro, Motoo
supporting information; experimental part, p. 4157 - 4161 (2009/03/11)
(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.
Regio- and enantioselective synthesis of allylic fluorides by electrophilic fluorodesilylation of allyl silanes
Greedy, Benjamin,Paris, Jean-Marc,Vidal, Thierry,Gouverneur, Veronique
, p. 3291 - 3294 (2007/10/03)
Enantiopure N-fluorocinchona alkaloids promoted the electrophilic fluorodesilylation of allyl silanes in a conceptually new approach to the regio- and enantioselective formation of allylic fluorides (see scheme). Excellent conversions were observed in these reactions, which afforded the desired allylic fluorides with up to 96% ee.
