35342-94-0Relevant articles and documents
Iridium-Catalyzed Direct Amidation of Imidazoles at the C-2 Position with Isocyanates in the Presence of Hydrosilanes Leading to Imidazole-2-Carboxamides
Fukumoto, Yoshiya,Shiratani, Motohiro,Noguchi, Hikaru,Chatani, Naoto
supporting information, p. 3011 - 3018 (2021/03/03)
Regioselective coupling reaction of N -substituted imidazoles with isocyanates in the presence of a stoichiometric amount of hydrosilanes catalyzed by Ir 4(CO) 12to give imidazole-2-carboxamides is reported. Imidazoles bearing an (O -silyl)carboximidate group at the 2-position appear to be initially formed in the reaction; these are then hydrolyzed to the final products in situ. The addition of the hydrosilane was essential for the catalytic reaction to proceed. Substituents on the imidazole ring had no effect on the reaction, except for certain bulky substituents such as tBu and Ph groups at the 4-position. Triazoles such as 4-methyl-4 H -1,2,4-triazole and 1-methyl-1 H -1,2,4-triazole were also applicable to this C-H amidation, and the latter reaction proceeded regioselectively at the carbon atom between the sp 3and sp 2nitrogen atoms of the ring, and not between the two sp 2nitrogen atoms.
α-nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid
Lam, Patrick Y.S.,Deudon, Sophie,Hauptman, Elisabeth,Clark, Charles G.
, p. 2427 - 2429 (2007/10/03)
Heteroarylcarboxamides containing α-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organ
