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- Title
Palladium-Catalysed Carbo- and Hydroamination of Allenyl Ethers and Aminoallenes: Available Entry to Nitrogen-Containing Benzo-Fused Rings.
- Authors
Gazzola, Silvia; Beccalli, Egle M.; Bernasconi, Alice; Borelli, Tea; Broggini, Gianluigi; Mazza, Alberto
- Abstract
The Pd-catalysed reactions of allenyl ethers and allenylamines derived from commercially available o-aminophenols and o-nitroaniline have been studied. Using a wide variety of aryl- and heteroaryl halides, carboamination of the allenes led to sequential C-C and C-N bond formation. Both carbo- and hydroamination processes resulted in the formation of nitrogen-containing benzo-fused rings. In the case of aminoallenes arising from o-phenylenediamine, the regioselectivity of the cyclization step was strongly dependent on the protecting group tethered to the nitrogen atoms, allowing the formation of five- and seven-membered rings.
- Subjects
PALLADIUM; HYDROAMINATION; ETHER derivatives; ALLENE derivatives; NITROANILINE
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 26, p4534
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600720