135983-08-3Relevant academic research and scientific papers
Base-Promoted Coupling of Carbon Dioxide, Amines, and Diaryliodonium Salts: A Phosgene- and Metal-Free Route to O-Aryl Carbamates
Xiong, Wenfang,Qi, Chaorong,Peng, Youbin,Guo, Tianzuo,Zhang, Min,Jiang, Huanfeng
supporting information, p. 14314 - 14318 (2015/10/05)
A phosgene- and metal-free synthesis of O-aryl carbamates is realized through a three-component coupling of carbon dioxide, amines and diaryliodonium salts. The reaction only requires a base as the promoter, providing access to a diverse array of O-aryl c
N,N-diethyl O-carbamate: Directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner
Antoft-Finch, Aurora,Blackburn, Tom,Snieckus, Victor
supporting information; experimental part, p. 17750 - 17752 (2010/03/25)
(Chemical Equation Presented) The first Suzuki-Miyaura cross-coupling of an aryl O-carbamate, a versatile and powerful directed metalation group (DMG) in directed ortho metalation (DoM) chemistry, is described using the inexpensive, bench-stable catalyst NiCl2(PCy3)2. Broad synthetic scope and good efficiency are demonstrated for aryl and heteroaryl O-carbamates. The role of water and hydrolysis equilibrium between free boronic acid and boroxine was established to be a crucial parameter for this transformation. When combined with DoM and traditional Pd-catalyzed Suzuki-Miyaura strategies, the methodology offers concise routes to uniquely substituted molecules, avoiding the need for protection/deprotection of the phenol and the use of strongly nucleophilic cross-coupling partners.
