تفاعل #1355841

ord-f94cd929735241b8ba688717e6320b8a

معادلة التفاعل

C#Cc1ccccc1
phenylacetylene
c1ccc(P(c2ccccc2)c2ccccc2)cc1
PPh3
Brc1ccc(C#C[c-]2cccc2)cc1.Brc1ccc(C#C[c-]2cccc2)cc1.[Fe+2].[Fe+2].c1cc[cH-]c1.c1cc[cH-]c1
1-(ferrocenylethynyl)-4-bromobenzene
Brc1ccc(C#C[c-]2cccc2)cc1.Brc1ccc(C#C[c-]2cccc2)cc1.[Fe+2].[Fe+2].c1cc[cH-]c1.c1cc[cH-]c1
1-(ferrocenylethynyl)-4-bromobenzene 1-(Ferrocenylethynyl)-4-bromobenzene
C(#Cc1ccc(C#C[c-]2cccc2)cc1)c1ccccc1.[Fe+2].c1cc[cH-]c1
1-(Ferrocenylethynyl)-4-(phenylethynyl)benzene

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىreaction
  2. 2
    أخرىat 60° C
  3. 3
    أخرىThe residue was purified

الإجراء التجريبي

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%.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07198771B2uspto-grants-2007_04