Alkyne-enol ether cross-metathesis in the presence of CuSO(4): direct formation of 3-substituted crotonaldehydes in aqueous medium.
An efficient synthesis of 3-substituted crotonaldehydes via alkyne-enol ether cross-metathesis in the presence of CuSO(4) and in aqueous medium was developed. Crotonaldehydes were obtained in good yields from terminal aryl-alkynes as well as from terminal alkyl-alkynes. All of the reactions were carried out under microwave irradiation and were completed in a few minutes. Water was used as the cosolvent, making this approach safer, economic, and desiderable from an enviromental point of view.
Castagnolo
Daniele
D
Dipartimento Farmaco Chimico Tecnologico, Universita degli Studi di Siena, Via A. de Gasperi 2, 53100 Siena, Italy.
Botta
Lorenzo
L
Botta
Maurizio
M
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D019327:Copper Sulfate / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012996:Solutions; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014867:Water
D000447:Aldehydes; D000475:Alkenes; D000480:Alkynes; D004987:Ethers; D012996:Solutions; D014867:Water; C012796:2-butenal; D019327:Copper Sulfate