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From Ynamides to Highly Substituted Benzo[ b ]furans: Gold(I)‐Catalyzed 5 ‐endo‐dig ‐Cyclization/Rearrangement of Alkylic Oxonium Intermediates
Author(s) -
Blanco Jaimes Maria Camila,
Weingand Vanessa,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301595
Subject(s) - oxonium ion , alkyl , chemistry , aryl , amine gas treating , alkylation , intermolecular force , stereochemistry , catalysis , group (periodic table) , medicinal chemistry , crystal structure , dig , molecule , organic chemistry , ion , computer security , computer science
A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross‐coupling/amidation sequence. The gold‐catalyzed conversion of these substrates combined both CO and CC formation steps, thus providing benzofurans with amine functionalities at the 2‐position and alkyl groups at the 3‐position. Cross‐over experiments showed that the alkyl‐migration step was an intermolecular process. X‐ray crystal‐structure analysis of two of the products supported our structural assignment. In some cases, the corresponding benzofurans without the alkyl group at the 3‐position were obtained as side‐products, which were formed through a competing protodeauration process.