July 2009
One-Pot Synthesis of Substituted Quinolines in Fluorous Media
799
Table 2
(Continued)
Entry
9
Electron-rich olefins
Anilines
Product
Yield (%)b
65
10
73
a The reaction condition: Hf(NPf)4 (0.041 g, 0.01 mmol), benzaldehyde (0.133 g, 1.2 mmol), aniline (1.2 mmol) and electron-rich olefins (1 mmol),
DCE (2 mL) and perfluorodecalin (C10F18, cis and trans-mixture, 2 mL), 80ꢀC, 24 h; DDQ, 0.454 g, 2 mmol.
b Isolated yields base on the starting alcohol.
[5] Combes, A. Compt Rend 1888, 106, 14.
1.2 mmol), and allyltriisopropylsilane (0.198 g, 1 mmol) in the
presence of Hf(NPf)4 (0.041 g, 0.01 mmol) in DCE (2 mL) and
perfluorodecalin(C10F18, cis and trans-mixture, 2 mL). The
mixture was stirred at 80ꢀC for 24 h, then the mixture was
cooled to ambient temperature, followed by addition of DDQ
(0.454 g, 2 mmol), and the reaction mixture was stirred in the
same temperature for 10 min. Then, the fluorous layer on the
bottom was separated for the next reaction. The reaction mix-
ture (organic phase) was filtered through a short pad of celite.
The organic layer was added saturated aqueous solution of
NaHCO3, and the aqueous phase was extracted twice with
CHCl3. Combined organic layers were washed with saturated
aqueous solution of NaHCO3, dried over MgSO4, filtered, and
concentrated in vacuo. The crude mixture was purified by col-
umn chromatography on silica gel column to afford the product
(eluent: CH2Cl2/MeOH ¼ 90/10). Selected data: 6-Trifluoro-
methyl-4-(triisopropylsilyl)methyl-2-phenylquinoline, colorless
solid; mp 103–105ꢀC; 1H NMR(500 MHz, CDCl3 ) d ¼ 1.10
(d, J ¼ 10.5 Hz, 18 H), 1.19–1.12 (m, 3H), 2.75 (s, 2H), 7.46–
8.22 (m, 8H), 8.37 (s, 1H). MS (EI) m/z 444 (Mþ).
[6] Pfitzinger, W. J Prakt Chem 1886, 33, 100.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet