Copper/Selectfluor‐System‐Catalyzed Dehydration–Oxidation of Tertiary Cyclo­alcohols: Access to β‐Substituted Cyclohex‐2‐enones, 4‐Arylcoumarins, and Bi­aryls. Issue 24 (20th July 2015)

• Record Type: Journal Article
• Authors: Ren, Shaobo; Zhang, Jian; Zhang, Jiahui; Wang, Heng; Zhang, Wei; Liu, Yunkui; Liu, Miaochang
• Is Part Of: European journal of organic chemistry. Issue 24(2015)
• Page Start: 5381
• Page End: 5388
• Publication Date: 2015-07-20
• Subjects: Synthetic methods -- Oxidation -- Copper -- Enones -- Oxygen heterocycles -- Biaryls; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500610
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A route to β‐substituted cyclohex‐2‐enones, 4‐arylcoumarins, and biaryls has been developed. This approach involves a one‐pot Cu 0 /Selectfluor‐catalyzed dehydration–oxidation of tertiary cycloalcohols. Thus, by using 2 equiv. of Selectfluor at 25 °C, the dehydration–oxidation of tertiary cyclohexanols and oxabenzocyclohexanols gave β‐substituted cyclohex‐2‐enones and 4‐arylcoumarins, respectively; whereas the dehydration–oxidation of tertiary cyclohexanols gave biaryls as the final products by using 2.5 equiv. of Selectfluor at 80 °C. Abstract : A route to β‐substituted cyclohex‐2‐enones, 4‐arylcoumarins, and biaryls has been developed. This approach involves a one‐pot Cu 0 /Selectfluor‐catalyzed dehydration–oxidation of tertiary cycloalcohols.