Copper‐Catalyzed Cross Dehydrogenative Coupling of N, N‐Disubstituted Formamides and Phenols: A Direct Access to Carbamates. Issue 2 (30th January 2015)

• Record Type: Journal Article
• Authors: Ali, Wajid; Rout, Saroj K.; Guin, Srimanta; Modi, Anju; Banerjee, Arghya; Patel, Bhisma K.
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 2/3(2015)
• Page Start: 515
• Page End: 522
• Publication Date: 2015-01-30
• Subjects: carbamates -- CH activation -- copper catalysis -- cross dehyrogenative coupling; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400659
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :