Co2(CO)8 catalyzed Pauson-Khand reaction under microwave irradiation

Synlett

Volumn , Issue 12, 2002, Pages 2023-2026

  Fischer, Stefan ^a   Groth, Ulrich ^a   Jung, Marc ^a   Schneider, Andreas ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Catalysis; Cobalt; Cycloaddition; Microwave; Pauson Khand reaction

Indexed keywords

ALKENE; ALKYNE; CARBON MONOXIDE;

ACCELERATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; CYCLOADDITION; MICROWAVE IRRADIATION; PAUSON KHAND REACTION;

EID: 0036456417     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35561     Document Type: Article

References (45)

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35. 6-alkyne complexes, see: (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. (b) Melikyan, G. G.; Nicholas, K. M. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; Wiley VCH: Weinheim, 1995, Chap. 4, 99-138. (c) Fischer, S. Synlett 2002, 1558.
36. 6-alkyne complexes, see: (a) Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207. (b) Melikyan, G. G.; Nicholas, K. M. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; Wiley VCH: Weinheim, 1995, Chap. 4, 99-138. (c) Fischer, S. Synlett 2002, 1558.
37. It should be stated that low boiling solvents usually cannot be heated to 200 °C but in our case the desired temperature could be reached in all cases except dichloromethane, which reached a maximum at 140 °C.
38. All experiments were preformed using a Smith Synthesizer from Personal Chemistry. For a detailed instrument description, see: Stadler, A.; Kappe, C. O. Comb. Chem. 2001, 3, 624.
39. 2 catalyzed C-P cross-coupling reaction: Stadler, A.; Kappe, C. O. Org. Lett. 2002, 4, 3541.
40. When conventional heating of the sealed vessel was provided under identical conditions the yield did not exceed 40% even after 4 h.
41. 8 were added under an inert gas atmosphere in a glove box and sealed with a Teflon septum and an aluminum crimp top. After the addition of 2 mL toluene (freshly distilled from sodium), 220 μL (2 mmol) phenylacetylene 2 and finally 275 μL (2.4 mmol, 1.2 equiv) cyclohexylamine were added through the Teflon septum. The vessel was then heated to 100 °C under microwave irradiation using the Smith Synthesizer (monomode microwave cavity at 2.45 GHz; temperature control by automated adjustment of irradiation power in a range from 0 to 300 W). After 300 s the vial was cooled to r.t. by gas jet cooling. The reaction mixture was then subjected to a typical aqueous workup. The dried organic phase was then liberated from solvent and purified by flash chromatography on silica eluting with EtOAc/petroleum ether to give 363 mg (1.62 mmol, 81%) of exo-3.
42. 3, 100 MHz): δ = 210.7, 156.5, 155.4, 54.1, 47.7, 38.9, 37.9, 30.8, 29.0, 28.3, 24.5, 21.5, 21.2.
43. 3, 100 MHz): δ = 210.7, 156.5, 155.4, 54.1, 47.7, 38.9, 37.9, 30.8, 29.0, 28.3, 24.5, 21.5, 21.2.
44. 3, 100 MHz): δ = 210.7, 156.5, 155.4, 54.1, 47.7, 38.9, 37.9, 30.8, 29.0, 28.3, 24.5, 21.5, 21.2.
45. 3, 100 MHz): δ = 210.7, 156.5, 155.4, 54.1, 47.7, 38.9, 37.9, 30.8, 29.0, 28.3, 24.5, 21.5, 21.2.