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Copper/Selectfluor‐System‐Catalyzed Dehydration–Oxidation of Tertiary Cycloalcohols: Access to β‐Substituted Cyclohex‐2‐enones, 4‐Arylcoumarins, and Biaryls
Author(s) -
Ren Shaobo,
Zhang Jian,
Zhang Jiahui,
Wang Heng,
Zhang Wei,
Liu Yunkui,
Liu Miaochang
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500610
Subject(s) - selectfluor , chemistry , dehydration , cyclohexanol , organic chemistry , catalysis , medicinal chemistry , biochemistry
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.