Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction

A new method has been developed for the cross-coupling of aryl halides with β-chloroalkyl aryl ketones and their ester and amide analogs through a domino dehydrochlorination/Pd(OAc)2- catalyzed Heck reaction sequence. The enone intermediates generated in situ reduced the occurrence of side reactions and therefore enhanced the efficiency of the reaction. This reaction exhibited good tolerance to various functional groups on both substrates and provides rapid access to a wide range of chalcone derivatives.

Graphical AbstractEfficient cross-coupling of aryl halides with β-chloroalkyl aryl ketones and their ester and amide analogs through a novel domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction has been developed. The new strategy uses in-situ generated enones as the reaction intermediates to reduce the occurrence of side reactions and enhance the reaction efficiency. This new protocol represents a concise method for the synthesis of chalcones.Figure optionsDownload as PowerPoint slide