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Copper‐Catalyzed Cross Dehydrogenative Coupling of N , N ‐Disubstituted Formamides and Phenols: A Direct Access to Carbamates
Author(s) -
Ali Wajid,
Rout Saroj K.,
Guin Srimanta,
Modi Anju,
Banerjee Arghya,
Patel Bhisma K.
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400659
Subject(s) - chemistry , formamides , catalysis , phenols , copper , benzothiazole , quinoline , functional group , organic chemistry , combinatorial chemistry , medicinal chemistry , polymer
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, CO bond formation takes place via a cross dehydrogenative coupling (CDC) between the formyl CH of dialkylformamide and phenolic OH in the presence of copper(II)acetate/aqueous tert ‐butyl 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.