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From Ynamides to Highly Substituted Benzo[ b]furans: Gold(I)-Catalyzed 5 -endo-dig-Cyclization/Rearrangement of Alkylic Oxonium Intermediates.
- Source :
-
Chemistry - A European Journal . Sep2013, Vol. 19 Issue 37, p12504-12511. 8p. - Publication Year :
- 2013
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 19
- Issue :
- 37
- Database :
- Academic Search Index
- Journal :
- Chemistry - A European Journal
- Publication Type :
- Academic Journal
- Accession number :
- 90055618
- Full Text :
- https://doi.org/10.1002/chem.201301595