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Synthesis of Alkynyl Ketones by Sonogashira Cross-Coupling of Acyl Chlorides with Terminal Alkynes Mediated by Palladium Catalysts Deposited over Donor-Functionalized Silica Gel

Publication at Faculty of Science |
2020

Abstract

Palladium catalysts deposited over silica gel bearing simple amine (-Si(CH2)3NH2) and composite functional amide pendants equipped with various donor groups in the terminal position (-Si(CH2)3NHC(O)CH2Y, Y = SMe, NMe2 and PPh2) were prepared and evaluated in Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes to give 1,3-disubstituted prop-2-yn-1-ones. Generally, the catalysts showed good catalytic activity in the reactions of aroyl chlorides with aryl alkynes under relatively mild reaction conditions even without adding a copper co-catalyst.

However, their repeated use was compromised by a significant loss of activity after the first catalytic run.