Lewis Acid Catalyzed Reaction of Aromatic Vinyl Halides with Aromatic Aldehydes: A Novel Aldol-type Condensation Mimic

In the presence of catalytic amounts of Lewis acid, aromatic α-vinyl halides readily undergo reaction with aromatic aldehydes at ambient temperatures to give a variety of substituted trans-chalcones in moderate to excellent yields. These compounds are potentially useful synthetic intermediates for organic synthesis as well as compounds of significance in terms of their ability to exhibit a wide spectrum of biological activity. This is the first reported example in which haloalkenyl derivatives other than metallooxyalkenes can participate in the Mukaiyama-aldol type carbon-carbon formation reaction.

Lewis acid - catalysis - α-halostyrenes - aromatic aldehydes - substituted trans-chalcones