Phenylacetylene → HCID 178436208, compound

HRID 2180898Notes

Reaction equation

HRID 2180898 reaction equation
[C-:1]1([C:6]#[C:7][C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20].[C-]1([C:26]#[C:27][C:28]2[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=2)C=CC=C1.[CH-]1C=CC=C1.[Fe+2].C1(C#C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>O1CCCC1.N1C=CC=CC=1.C(NC(C)C)(C)C.[Pd].CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[C-:1]1([C:6]#[C:7][C:8]2[CH:13]=[CH:12][C:11]([C:26]#[C:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20]

Participants

10

Reactant 3

HCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 178419387HCID 178419387, compound

Product 1

HCID 178436208HCID 178436208, compound

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalyst2×HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 1049PyridineSolventHCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(Ferrocenylethynyl)-4-(phenylethynyl)benzene 308 was prepared following the general procedure found in General Procedure for the Palladium-Catalyzed Cross-Coupling Reaction 1 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%.

Workup

  1. customreaction
  2. customat 60° C
  3. customThe residue was purified

Sources & evidence

ORD record
ord-879c236e628345a69a6d850c923dbf93
Source dataset
uspto-grants-2005_05
Patent number
US06890504B2

Reaction notes

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