Copper-Catalyzed Cross Dehydrogenative Coupling of N,N-Disubstituted Formamides and Phenols: A Direct Access to Carbamates

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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-02, Vol.357 (2-3), p.515-522
Main Authors: Ali, Wajid, Rout, Saroj K., Guin, Srimanta, Modi, Anju, Banerjee, Arghya, Patel, Bhisma K.
Format: Article
Language:English
Subjects:
carbamates
Chelation
copper catalysis
cross dehyrogenative coupling
CH activation
Dehydrogenation
Derivatives
Joining
Phenols
Quinoline
Synthesis
Tolerances
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Summary: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 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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400659