Reaction of Tin(II) Hydride with Compounds Containing Aromatic C−F Bonds

The reaction of the stable tin(II) hydride LSnH ( 1; L = CH{(CMe) 2 (2,6- i Pr 2 C 6 H 3 N) 2 }) with fluorinated aromatic compounds is described. The reaction of 1 with equivalent amounts of pentafluorobenzophenone (PhCOC 6 F 5 ) and perfluorobenzophenone (C 6 F 5 COC 6 F 5 ), respectively, in toluene at room temperature, leads to the nucleophilic addition products LSnOCHPh(C 6 F 5 ) ( 3 ) and LSnOCH(C 6 F 5 ) 2 ( 4 ) as well as to metathesis products PhCO(4-C 6 F 4 H) ( 5 ) and C 6 F 5 CO(4-C 6 F 4 H) ( 6 ) with the formation of LSnF ( 2 ). In contrast, the reactions of 4-fluorobenzophenone (PhCO-4-C 6 H 4 F) and pentafluorobenzaldehyde (C 6 F 5 CHO) with 1 provide the tin(II) alkoxide products LSnOCHPh(4-C 6 H 4 F) ( 7 ) and LSnOCH 2 C 6 F 5 ( 8 ) as a result of nucleophilic addition of hydride to the carbonyl group. Moreover, 1 was treated with C 6 F 6 in C 6 D 6 at room temperature and after 24 h the 1 H, 19 F, and 119 Sn NMR spectra were recorded, which indicated the appearance of LSnF ( 2 ), C 6 F 5 H ( 9 ), and LSnC 6 F 5 ( 10 ). Formation of compound 10 was further confirmed by its synthesis from LSnCl and C 6 F 5 Li.