Rhodium-Catalyzed Annulation of ortho-Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts

Andrés Seoane, Cezar Comanescu, Noelia Casanova, Rebeca García-Fandiño, Xabier Diz, José L. Mascareñas, Moisés Gulías

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Resum

o-Alkenyl N-triflylanilides underwent rhodium(III)-catalyzed oxidative annulations with alkynes to produce different types of naphthylamides in a process which involves the cleavage of two C−H bonds. Remarkably, besides formal dehydrogenative (4C+2C) cycloadducts, the reaction also produces variable amounts of isomeric naphthylamides, whose formation requires a formal migration of the alkenyl moiety from the ortho to the meta position of the anilide. The annulation reaction can be efficiently carried out in the absence of external oxidants, such as Cu(OAc) 2 .

Idioma originalAnglès
Pàgines (de-a)1700-1704
Nombre de pàgines5
RevistaAngewandte Chemie - International Edition
Volum58
Número6
DOIs
Estat de la publicacióPublicada - 4 de febr. 2019
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