Carbon-Carbon Bond Forming Reactions by using Bistrifluoro-methanesulfonimide

Abstract

Bistrifluoromethanesulfonimide has been used to catalyze C-C bond forming reactions such as Friedel-Crafts, Mukaiyama, 1,2-addition and 1,4-addition as well as C-glycosidation reactions.

Key words

bistrifluoromethanesulfonimide - Friedel-Crafts reactions - Mukaiyama reaction - 1,2-addition - 1,4-addition - C-glycosidation

References

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  Representative Procedure of the TFSI-H catalyzed Mukaiyama cross-aldol reaction: To a solution of 11 (851 mg, 5.00 mmol) and 2,2-dimethoxypropane (624 mg, 6.00 mmol) in CH₂Cl₂ at -78 °C, was added dropwise TFSI-H (500 µL, 0.5 M solution in CH₂Cl₂, 0.025 mmol, 5 mol%). After 30 min at -78 °C, the reaction mixture was poured into a sat. aq solution of NaHCO₃ and extracted with ether. The combined extracts were washed with brine, dried over MgSO₄, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (Cyclohexane/EtOAc: 90/10) to give 774 mg (91%) of 20 [18b] as a colorless oil.

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46

Determined by ¹H NMR.