85630-27-9Relevant academic research and scientific papers
Directed ortho-Metalation of Aryl Amides, O-Carbamates, and Methoxymethoxy Systems: Directed Metalation Group Competition and Cooperation
Miah, M. A. Jalil,Sibi, Mukund P.,Chattopadhyay,Familoni, Oluwole B.,Snieckus, Victor
, p. 447 - 454 (2017/12/15)
A systematic study on the competitive metalation of derivatives containing four directed metalation groups (DMGs), namely, Cl, OMe, methoxymethoxy (OMOM), and CONEt2, in comparison with the OCONEt2 DMG is described. In addition, the
Copper-catalyzed cross dehydrogenative coupling of N,N-disubstituted formamides and phenols: A direct access to carbamates
Ali, Wajid,Rout, Saroj K.,Guin, Srimanta,Modi, Anju,Banerjee, Arghya,Patel, Bhisma K.
, p. 515 - 522 (2015/03/05)
An efficient copper-catalyzed protocol has been developed for the synthesis of carbamates from dialkylformamides and phenols possessing directing groups such as benzothiazole, quinoline and formyl at the ortho-position. In this chelation assisted approach, C-O bond formation takes place via a cross dehydrogenative coupling (CDC) between the formyl C-H of dialkylformamide and phenolic O-H in the presence of copper(II)acetate/aqueous tertbutyl hydroperoxide. Under identical reaction conditions, salicylic acid derivatives underwent amidation with the carboxylic group rather than formamidation of the phenolic OH. The use of a cheap and environmentally benign catalyst along with the tolerance of a wide range of functional groups makes this an easy, phosgene-free route to carbamates. carbamates; C-H activation; copper catalysis; cross dehyrogenative coupling
The Directed Ortho Lithiation of O-Aryl Carbamates. An Anionic Equivalent of the Fries Rearrangement
Sibi, Mukund P.,Snieckus, Victor
, p. 1935 - 1937 (2007/10/02)
Ortho-Lithiated O-aryl carbamates 3 constitute new synthetic intermediates which by treatment with a variety of electrophiles lead to ortho-substituted carbamates 4 and by rearrangement provide salicylamides 6.
