Copper/Selectfluor‐System‐Catalyzed Dehydration–Oxidation of Tertiary Cyclo­alcohols: Access to β‐Substituted Cyclohex‐2‐enones, 4‐Arylcoumarins, and Bi­aryls

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

Modern metal-catalyzed and organocatalytic methods for synthesis of coumarin derivatives: a review

“…In 2015, a method with copper-catalyzed dehydrogenative oxidation was performed on oxabenzocyclohexanol derivatives 156 to produce 4-arylcoumarins 157 (Scheme 43). 108 In this method, copper in its base oxidation level was used as catalyst, along with selectfluor 158 as oxidant. The reaction proceeded in anhydrous MeCN as the solvent, in air and at ambient temperature.…”

Ultralow Loading Cobalt-Based Nanocatalyst for Benign and Efficient Aerobic Oxidation of Allylic Alcohols and Biobased Olefins

“…The allylic oxidation of olefins to directly produce α,β-unsaturated ketones is one of the most important transformations in the research of C–H bond activation. − α-Pinene is a common renewable bio-olefin and has received much attention in recent years. − The oxidation of α-pinene yields valuable products such as α-pinene oxide, campholenic aldehyde, verbenol, and verbenone. These products are key building blocks in the fields of natural products, biopharmaceuticals, flavors, and fragrances. , As an important α,β-unsaturated ketone, verbenone can be employed for the preparation of menthol, taxol, and vitamins A and E. , Also, it can be used as repellent of Dendroctonus valens LeConte, making great contributions to the protection of the forestry ecological environment.…”

A metal-free carbon catalyst for oxidative dehydrogenation of aryl cyclohexenes to produce biaryl compounds

“…Traditional ODH reactions are catalyzed by various transition metal and metal oxide catalysts like nickel ( 9 , 10 ), copper ( 11 , 12 ), palladium ( 11 , 13 ), platinum ( 14 , 15 ), and vanadium oxide ( 16 ). For example, the industrial production of styrene from ethylbenzene utilizes vanadium oxide as the catalyst, while Cu 0 /Selectfluor (commercialized fluorine donor) is employed for the ODH reaction of phenyl cyclohexene ( 17 ).…”