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Organic Letters

Volumn 10, Issue 3, 2008, Pages 365-368

Cu-catalyzed synthesis of symmetric group 6 (Fischer) bis-carbene complexes

(5) López Alberca, Maria P a Mancheño, María J a Fernández, Israel a Gómez Gallego, Mar a Sierra, Miguel A a

a UNIVERSIDAD COMPLUTENSE DE MADRID (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38949116593 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol702464r Document Type: Article

Times cited : (13)

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- The synthesis of complex 2a is representative: The Hay catalyst was prepared according to the literature (see ref 12, To the resulting catalyst was added dropwise a solution of the monocarbene in dry acetone. The mixture was stirred until the disappearance of monocarbene (checked by TLC, The reaction was quenched with water and filtered to eliminate the salts formed. The filtrate was extracted with diethyl ether. The combined organic phases were washed with HCl (5, and water, dried over MgSO4, and filtered. The solvent was eliminated and purification by column chromatography on silica gel afforded pure compound: 1H NMR (CDCl3) δ, 7.71-7.43 (m, 8H, 4.77 (q, J, 7.1 Hz, 4H, 1.60 (t, J, 7.1 Hz, 6H, 13C NMR (CDCl3) δ, 313.7, 225.7, 216.1, 135.8, 135.0, 133.2, 129.2, 122.6, 121.7, 91.4, 80.5, 76.0, 75.0, 15.0; IR (CHCl 3) v 2062, 1954, 1217, 775 cm-1. Anal. Caled for
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- Compound 8. A solution of 21 mg (0.24 mmol) of N,N'-dimethylurea in 20 mL of THF was added by syringe pump into a solution of 60 mg (0.08 mmol) of bis-carbene 2a in 80 mL of THF for 12 h. Then, the mixture was stirred for an additional 24 h at room temperature. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel affording 46 mg (69 , of compound 8: 1H NMR (CDCl3) δ 7.67-7.66 (m, 2H, 7.51-7.46 (m, 4H, 7.31-7.30 (m, 2H, 7.21 (s, 2H, 4.19 (s, 6H, 3.28 (s, 6H, 13C NMR (CDCl3) δ 261.4, 223.7, 217.3, 149.4, 141.2, 134.7, 132.3, 129.7, 128.9, 124.5, 123.0, 102.8, 80.6, 75.5, 45.9, 35.7; IR (CHCl 3) v 2053, 1910, 1696, 1660 cm-1. Anal. Caled for C38H22Cr2N4O12: C, 54.95; H, 2.67. Found: C, 55.22;H, 2.40. Compound 9. A solution of 50 mg (0.06 mmol) of bis-carbene
- 4: C, 70.18; H, 4.63. Found: C 70. 32; H, 4. 80.

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