7464-55-3Relevant articles and documents
Cationic N-Heterocyclic Carbene Copper-Catalyzed [1,3]-Alkoxy Rearrangement of N-Alkoxyanilines
Nakamura, Itaru,Jo, Takeru,Ishida, Yasuhiro,Tashiro, Hiroki,Terada, Masahiro
supporting information, p. 3059 - 3062 (2017/06/23)
The [1,3]-alkoxy rearrangement reactions of N-alkoxyanilines were efficiently catalyzed by cationic N-heterocyclic carbene (NHC)-Cu catalysts in affording 2-alkoxyaniline derivatives in good to excellent yields with high functional group compatibility. For N-alkoxyanilines having an electron-withdrawing substituent at the meta-position, the alkoxy group selectively migrated to the more hindered ortho-position. In contrast, the alkoxy group migrated to the less hindered ortho-position for N-alkoxyanilines having an electron-donating substituent. Mechanistic studies suggest that the rearrangement reactions proceed via an intramolecular route.
The synthesis of N-arylated amides via copper(II) triflate-catalyzed direct oxygenation and N-arylation of benzylamines with aryl iodides
Xu, Mei,Zhang, Xiao-Hong,Shao, Yin-Lin,Han, Jiang-Sheng,Zhong, Ping
supporting information, p. 2665 - 2670,6 (2012/12/12)
An efficient approach for the synthesis of N-arylated amides by copper(II) triflate-catalyzed direct oxygenation and N-arylation reaction of benzylamines with aryl iodides is reported. Various benzylamines and aryl iodides can participate in the reaction, providing a series of N-arylated amides in moderate to good yields.
Palladium-Imidazolium N-Heterocyclic Carbene-Catalyzed Carbonylative Amidation with Boronic Acids, Aryl Diazonium Ions, and Ammonia
Ma, Yudao,Song, Chun,Chai, Qiang,Ma, Changqin,Andrus, Merritt B.
, p. 2886 - 2889 (2007/10/03)
Aryl diazonium tetrafluoroborates have been coupled with arylboron compounds, carbon monoxide, and ammonia to give aryl amides in high yields. A saturated N-heterocyclic carbene (NHC) ligand, H2IPr was used with palladium(II) acetate to give the active catalyst. A mechanism is proposed for this novel four-component coupling reaction.