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

Abstract

The reaction of the stable tin(II) hydride LSnH (1; L = CH{(CMe)(2)(2,6-iPr(2)C(6)H(3)N)(2)}) with fluorinated aromatic compounds is described. The reaction of 1 with equivalent amounts of pentafluorobenzophenone (PhCOC6F5) and perfluorobenzophenone (C6F5COC6F5), respectively, in toluene at room temperature, leads to the nucleophilic addition products LSnOCHPh(C6F5) (3) and LSnOCH(C6F5)(2) (4) as well as to metathesis products PhCO(4-C6F4H) (5) and C6F5CO(4-C6F4H) (6) with the formation of LSnF (2). In contrast, the reactions of 4-fluorobenzophenone PhCO-4-C6H4F)CHPh(4-C6H4F) and pentafluorobenzaldehyde (C6F5CHO) with 1 provide the tin(II) alkoxide products LSnO-CHPh(4-C6H4F) (7) and LSnOCH2C6F5 (8) as a result of nucleophilic addition of hydride to the carbonyl group. Moreover, 1 was treated with C6F6 in C6D6 at room temperature and after 24 h the H-1, F-19, and Sn-119 NMR spectra were recorded, which indicated the appearance of LSnF (2), C6F5H (9), and LSnC6F5 (10). Formation of compound 10 was further confirmed by its synthesis from LSnCl and C6F5Li.