Fig. 2: Reaction development.
From: Regioselective fluorination of allenes enabled by I(I)/I(III) catalysis
A Optimization of reaction conditions. Standard reaction conditions: allene S1 (0.1 mmol), catalyst (30 mol%), amine•HF 1:5.0 (0.25 mL), DCM (0.25 mL), and Selectfluor® (0.20 mmol). Ethyl fluoroacetate was used as the internal standard. Conversions were determined by 1H NMR. Yields were determined by 19F NMR. The regioselectivity (branched versus linear) was >20:1 in all cases. B Influence of the amine:HF ratio on the transformation. C Control experiments. a 1.5 equiv. Selectfluor® was used. b Yields were determined by 1H NMR. The amine·HF mixtures were prepared based on commercially available NEt3·3HF and Py·9.23HF (Olah´s reagent). DCM dichloromethane, mCPBA meta-chloroperoxybenzoic acid.
