Metal‐free Dehydrogenation of Substituted Cyclohexanones to Phenols

The preparation of substituted phenols via a direct carbonyl desaturation is an intrinsic challenging task in modern synthetic chemistry. Herein, we develop a modular catalytic protocol for the synthesis of substituted phenols via the direct dehydrogenative aromatization of simple cyclohexanones in...

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Published inAdvanced synthesis & catalysis Vol. 365; no. 8; pp. 1158 - 1164
Main Authors Leng, Li‐Jing, Zhang, De‐Long, Zhang, Liang, Lin, Xiao‐Long, Cai, Tian, Tan, Jian‐Ping, Luo, Qun‐Li
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 25.04.2023
Wiley Subscription Services, Inc
Subjects
Carbonyls
Catalysis
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Cyclohexanone
Dehydrogenation
Desaturation
Iodine
Oxidation
Phenols
Physical Sciences
Raw materials
Reagents
Science & Technology
Substitutes
Substrates
Dehydrogenation
CONVERSION
Phenols
ENONES
Oxidation
Catalysis
CATALYZED AEROBIC DEHYDROGENATION
AROMATIZATION
ALPHA-IODINATION
Iodine
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Summary:The preparation of substituted phenols via a direct carbonyl desaturation is an intrinsic challenging task in modern synthetic chemistry. Herein, we develop a modular catalytic protocol for the synthesis of substituted phenols via the direct dehydrogenative aromatization of simple cyclohexanones in a metal‐free manner. A broad variety of substrates bearing an assortment of functional substituent groups are compatible with this protocol. Preliminary mechanistic investigations revealed that the reaction underwent a hydride leaving mechanism in the presence of a catalytic amount of tetrabutylammonium iodide. The current approach features simple operation, low reagent cost and green conditions. Insight gained from our studies is expected to advance general efforts towards the green synthesis of structurally diverse phenols via readily available raw materials, offering an alternative strategy for the carbonyl desaturation in organic synthesis.
Bibliography:These authors contributed equally to this work.
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300005