Coupling–Isomerization synthesis of chalcones

…, M Ansorge, TJJ Mueller

Index: Braun, Roland U.; Ansorge, Markus; Mueller, Thomas J. J. Chemistry - A European Journal, 2006 , vol. 12, # 35 p. 9081 - 9094

Full Text: HTML

Citation Number: 68

Abstract

Abstract The Sonogashira coupling of electron-deficient (hetero) aryl halides 1 and (hetero) aryl or alkenyl 1-propargyl alcohols 2 does not terminate at the stage of the expected internal propargyl alcohols, but rather gives rise to the formation of α, β-unsaturated ketones 3 with a variety of acceptor substituents. This new domino reaction, a coupling– isomerization reaction (CIR), can be rationalized as a sequence of rapid Pd/Cu-catalyzed ...