The fluorine-aluminum interaction

The fluorine-aluminum bond energy is 159 kcal/mol, which is the second strongest of the fluorine-metal bonds (F—Ba, F—Li, F—Ti, F—Si = 140, 138, 136, 132 kcal/mol, respectively) and so both atoms interact strongly with each other. Bis (2,2,6,6-tetramethylpiperidino)aluminum halides (X = Cl, Br, I, and F) have been synthesized 

The C—F bond activation with aluminum reagents has been extensively employed for the synthesis of C-glycosides (8). Benzyl protected 2-fluorogycoside (7) was methylated and cyanated with high a-preference under mild conditions [3]. Likewise, alkenyl transfer was 

Coordination between fluorine and aluminum also controls the stereoselective reduction of a, a -difluoro- (3 -hydroxyketones (15). The reduction of 15 with DIBAL-H in THF-hexane 

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