Copper-Catalyzed Oxidative Coupling of Formamides with Salicylaldehydes: Synthesis of Carbamates in the Presence of a Sensitive Aldehyde Group

• Published in: Journal of organic chemistry Vol. 79; no. 7; pp. 3206 - 3214
• Main Authors: Barve, Balaji D, Wu, Yang-Chang, El-Shazly, Mohamed, Chuang, Da-Wei, Cheng, Yuan-Bin, Wang, Jeh-Jeng, Chang, Fang-Rong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.04.2014; Amer Chemical Soc
• Subjects: Aldehydes - chemistry; Carbamates - chemical synthesis; Carbamates - chemistry; Catalysis; Chemistry; Chemistry, Organic; Copper - chemistry; Formamides - chemistry; Molecular Structure; Oxidative Coupling; Physical Sciences; Science & Technology; H BOND ACTIVATION; REARRANGEMENT; ALCOHOLS; N,N-DIMETHYLFORMAMIDE; AMINES; EFFICIENT; ACCESS; C-H; CARBOXYLIC-ACIDS; WATER

A diverse library of novel carbamates was synthesized utilizing copper-catalyzed oxidative C–O coupling of formamides and salicylaldehydes. Sensitive aldehyde groups remained intact in the presence of an oxidant and a transition-metal salt. Salicylaldehydes bearing electron-donating, electron-withdr...