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Palladium‐Catalysed Carbo‐ and Hydroamination of Allenyl Ethers and Aminoallenes: Available Entry to Nitrogen‐Containing Benzo‐Fused Rings
Author(s) -
Gazzola Silvia,
Beccalli Egle M.,
Bernasconi Alice,
Borelli Tea,
Broggini Gianluigi,
Mazza Alberto
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600720
Subject(s) - hydroamination , chemistry , regioselectivity , palladium , aryl , amination , nitrogen , medicinal chemistry , halide , organic chemistry , catalysis , alkyl
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.