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Rhodium‐Catalyzed Annulation of ortho ‐Alkenyl Anilides with Alkynes: Formation of Unexpected Naphthalene Adducts
Author(s) -
Seoane Andrés,
Comanescu Cezar,
Casanova Noelia,
GarcíaFandiño Rebeca,
Diz Xabier,
Mascareñas José L.,
Gulías Moisés
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811747
Subject(s) - annulation , chemistry , rhodium , adduct , medicinal chemistry , catalysis , moiety , naphthalene , cleavage (geology) , bond cleavage , stereochemistry , organic chemistry , geotechnical engineering , fracture (geology) , engineering
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 .