Rh(III)-Catalyzed Decarboxylative Coupling of Acrylic Acids with Unsaturated Oxime Esters: Carboxylic Acids Serve as Traceless Activators
2014; American Chemical Society; Volume: 136; Issue: 7 Linguagem: Inglês
10.1021/ja412444d
ISSN1943-2984
AutoresJamie M. Neely, Tomislav Rovis,
Tópico(s)Catalytic Alkyne Reactions
Resumoα,β-Unsaturated carboxylic acids undergo Rh(III)-catalyzed decarboxylative coupling with α,β-unsaturated O-pivaloyl oximes to provide substituted pyridines in good yield. The carboxylic acid, which is removed by decarboxylation, serves as a traceless activating group, giving 5-substituted pyridines with very high levels of regioselectivity. Mechanistic studies rule out a picolinic acid intermediate, and an isolable rhodium complex sheds further light on the reaction mechanism.
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