The synthesis of phenyl carbamates catalyzed by iron (II) bromide: An oxidative approach for cross-coupling of phenols with formamides
The carbamate group is a key structural motif in many approved drugs and pro-drugs. There is increasing use of carbamates in the medicinal chemistry and agrochemical industry. We present, reagents and chemical methodologies for the synthesis of carbamates, and recent applications. The direct coupling of simple phenols with mono- and di-alkyl formamides provided the phenylcarbamate products.
C-O/C-H Coupling of Polyfluoroarenes with Aryl Carbamates by Cooperative Ni/Cu Catalysis
Cross-coupling of polyfluoroarenes with aryl carbamates through the cleavage of both sp2 C-O and C-H bonds is reported. The reaction conditions are simple, and only transition-metal catalysts and ligands are essential. Mechanistic studies indicated that Ni catalyst played an important role in activating C-O bond, while the Cu one in activating C-H Bond. The developed system proved to be effective for cross-coupling of terminal alkynes with aryl carbamates.
Ligand-assisted copper-catalyzed oxidative cross-coupling of simple phenols with formamides for the synthesis of carbamates
An oxidative approach for the synthesis of phenyl carbamates has been achieved by ligand-assisted copper-catalyzed cross-dehydrogenative coupling (CDC) of phenols with formamides. The direct coupling of simple phenols with mono- and dialkyl formamides pro
Room-temperature Pd-catalyzed C-H chlorination by weak coordination: One-pot synthesis of 2-chlorophenols with excellent regioselectivity
A room-temperature Pd(ii)-catalyzed regioselective chlorination reaction has been developed for a facile one-pot synthesis of a broad range of 2-chlorophenols. The reaction demonstrates an excellent regioselectivity and reactivity for C-H chlorination. This reaction represents one of the rare examples of mild C-H functionalization at ambient temperature.
Sun, Xiuyun,Sun, Yonghui,Zhang, Chao,Rao, Yu
supporting information
p. 1262 - 1264
(2014/02/14)
A general approach towards catechol and pyrogallol through ruthenium- and palladium-catalyzed C-H hydroxylation by weak coordination
An efficient ruthenium(II)- and palladium(II)-catalyzed C-H hydroxylation of aryl carbamates has been developed for the facile synthesis of catechols and pyrogallols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by a gram-scale synthesis.
Yang, Xinglin,Sun, Yonghui,Chen, Zhang,Rao, Yu
supporting information
p. 1625 - 1630
(2014/06/09)
Rhodium-catalyzed selective C-H activation/olefination of phenol carbamates
Rh(III)-catalyzed ortho C-H activation/olefination of phenol carbamates has been developed. High regioselectivity is observed with a range of phenol carbamates enabling efficient coupling with acrylates and styrenes. This reaction exhibits different react
Gong, Tian-Jun,Xiao, Bin,Liu, Zhao-Jing,Wan, Jian,Xu, Jun,Luo, Dong-Fen,Fu, Yao,Liu, Lei
supporting information; experimental part
p. 3235 - 3237
(2011/08/22)
Nickel-catalyzed efficient and practical Suzuki-Miyaura coupling of alkenyl and aryl carbamates with aryl boroxines
(Figure Presented) Suzuki-Miyaura coupling of unactivated alkenyl carbamates Is described to construct polysubstituted olefins. The developed process is also suitable for heteroaromatic and even electron-rich aromatic carbamates.