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Organometallics

Volumn 26, Issue 21, 2007, Pages 5125-5128

Imidazolium-calix[4]arene molecular frameworks: Bis(N-heterocyclic carbenes) as bidentate ligands

(5) Dinarè, Immaculada a De Miguel, Cristina Garcia a Font Bardia, Mercè a Solans, Xavier a Alcalde, Ermitas a

a UNIVERSITY OF BARCELONA (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHEMICAL REACTIONS; LIGANDS; PALLADIUM COMPOUNDS; SALTS;

ARENE; IMIDAZOLIUM; MOLECULAR FRAMEWORKS; SUZUKI-MIYAURA REACTION;

ORGANOMETALLICS;

EID: 35348954371 PISSN: 02767333 EISSN: None Source Type: Journal
DOI: 10.1021/om7005722 Document Type: Article

Times cited : (32)

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27
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- Palladium(II) diacetate (0.037 g, 0.164 mmol) was added to a solution of bis(3-butyl-1-imidazolium)calix[4]arene dibromide (2a; 0.151 g, 0.151 mmol) in anhydrous dioxane (10 mL) under an argon atmosphere. The mixture was heated to 50°C for 1 h, followed by 110°C for 12 h. The resulting solution was evaporated to dryness, and the remaining black solid was dissolved in dichloromethane and filtered through a Celite pad. The solvent was eliminated, yielding the bis(N-butylcarbene) palladium(II) complex la as a yellow solid (0.180 g, 95, Anal. Caled for C54H 68-Br2N4O4Pd·CH 2Cl2·H2O: C, 52.09; H, 5.78; N, 4.34. Found: C, 51.86; H, 5.89, N, 3.97. 1H NMR (400 MHz, CDCl 3, δ 0.939-1.000 (m, 9H, H37,46 and H 52,58, 1-120 (t, 6H, 1.399-1.493 (m, 4H, 1.917-2.045 (m, 8H, 2.135-2.233 (m, 4H, 3.169 d, 4H, 3.700
- + requires 1022.9). Crystals suitable for X-ray crystallographic studies were grown in dichloromethane.

28
- 35348949173
- Palladium(II) diacetate (23.12 mg, 0.103 mmol) was added to a solution of bis[3-(2-propyl)butyl-1-imidazolium]calix[4]arene dibromide (2b; 0.099 g, 0.102 mmol) in anhydrous dioxane (10 mL) under an argon atmosphere in an oven-dried resealable tube, sealed with a Teflon valve. The mixture was heated to 50°C for 1 h, followed by 110°C for 12 h. The resulting solution was evaporated to dryness, and the remaining black solid was dissolved in dichloromethane and filtered through a Celite pad. The solvent was eliminated, yielding the bis(carbene) palladium(II) complex lb as a yellow solid (0.120 g, 96, Anal. Calcd for C52H64Br2N4O 4Pd: C, 58.08; H, 6.00; N, 5.21. Found C, 58.25; H, 6.10; N, 5.06. 1H NMR (400 MHz, CDCl3, δ 0.939 (t, 6H, 1.101 (t, 6H, 1.517 (d, 12H, 1.899-1.990 (m, 4H, 2.117-2.215 (m, 4H, 3.154 (d, 4H, 3.683 (t, 4H, 4.096 (t, 4H, 4.496 (d, 4H, 5.881-5.984 (m, 2H, 6.526 d, 2
- + requires 994.92).

29
- 35348962255
- Crystal/refinement data for 1a·CH2Cl2 (SC56H72Br2Cl4N4O 4Pd, Mr, 1273.20, size 0.2 × 0.1 × 0.1 mm, triclinic, space group P1, a, 11.615-(6) Å b= 11.840(5) Å, c, 23.718(10) Å, α, 103.00(3)°, β, 92.74-(3)°, γ, 112.08(2)°, F(000, 1304, V, 2913(2) Å3, T, 293(2) K, Dc(Z, 2, 1.451 Mg/m3, μ, 1.920 mm-1, refinement method full-matrix least squares on F 2, R1, 0.0492 (observed data with I > 2σI, wR2, 0.1225, GOF, 1.241
- 2, R1 = 0.0492 (observed data with I > 2σ(I)), wR2 = 0.1225, GOF = 1.241.

30
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- For recent examples of bis(NHC)-Pd complexes, see: (a) Baker, M. V.; Brown, D. H.; Hesler, V. J.; Skelton, B. W.; White, A. H. Organometallics 2007, 26, 250-252.

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