反応 #1355841

反応方程式

phenylacetylene

PPh3

1-(ferrocenylethynyl)-4-bromobenzene

1-(ferrocenylethynyl)-4-bromobenzene 1-(Ferrocenylethynyl)-4-bromobenzene

→

1-(Ferrocenylethynyl)-4-(phenylethynyl)benzene

溶媒

tetrahydrofuran

pyridine

diisopropylamine

反応条件

後処理

1. 1
   その他reaction
2. 2
   その他at 60° C
3. 3
   その他The residue was purified

実験手順

1-(Ferrocenylethynyl)-4-(phenylethynyl)benzene 308 was prepared following the general procedure found in General Procedure for the Palladium-Catalyzed Cross-Coupling Reaction for the palladium-catalyzed coupling reaction using 500 mg (1.37 mmol) of 1-(ferrocenylethynyl)-4-bromobenzene 304, 210 mg (2.05 mmol) of phenylacetylene 306, 15.4 mg (0.0686 mmol) Pd(OAc)2, 53.9 mg (0.206 mmol) of PPh3, and 2.6 mg (0.0137 mmol) of CuI in 25 mL tetrahydrofuran, 5 mL pyridine and 5 mL diisopropylamine at 60° C. The residue was purified using a 5:1 hexane/CH2Cl2 solvent mixture to afford 385 mg (73%) of an orange-red solid, m.p. 198° C. Spectral data for 1-(ferrocenylethynyl)-4-(phenylethynyl)benzene 308: IR (cm−1, KBr): 3084 (C—H), 3056 (C—H), 2203 (C≡C), 1594 (C═C, benzene), 1517 (C═C, benzene), 1411 (C═C, ferrocene). H NMR (d in CDCl3): 7.51 (m, 2H), 7.45 (m, 4H), 7.33 (m, 3H), 4.50 (t, J=1.9 Hz, 2H), 4.24 (t, J=1.9 Hz, 2H), 4.23 (s, 5H). Analysis for 1-(ferrocenylethynyl)-4-(phenylethynyl)benzene 308 (C26H18Fe) Calcd: C, 80.84%; H, 4.70%. Found: C, 80.06%; H, 4.72%.

出典