Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 7, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200268
Keywords
alpha-amino ketone/ester; imidazo[1,2-a]pyridine; iodine; sp(3)-C-H amination; transition-metal-free
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Funding
- Young Backbone Teachers Fund of Henan Province [2021GGJS012]
- National Natural Science Foundation of China [81773570, 82130103, U1804283]
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An iodine-mediated direct sp(3) C-H amination reaction has been developed for the synthesis of nitrogen-containing compounds from readily available substrates under transition-metal-free conditions. This method is operationally simple and can be conveniently conducted on a large scale under mild reaction conditions.
An iodine-mediated direct sp(3) C-H amination reaction has been established for the synthesis of nitrogencontaining compounds from readily available substrates under transition-metal-free conditions. The I-2-promoted amination of ketones/esters with cyclic or acyclic secondary amines using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a base led to the formation of various alpha-amino ketone or ester products including two medications, Amfepramone and Plavix. Sequential I-2-mediated sp(3) C-H amination and condensation of ketones with 2-aminopyridines in the presence of Na2CO3 produced a series of imidazo[1,2-alpha]pyridines and related fused imidazoles in a one-pot reaction. This synthetic method is operationally simple and can be conveniently conducted on a gram scale under mild reaction conditions.
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