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.
Dipartimento Farmaco Chimico Tecnologico, Universita degli Studi di Siena, Via A. de Gasperi 2, 53100 Siena, Italy.
Daniele
D
Castagnolo
Lorenzo
L
Botta
Maurizio
M
Botta
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