Catalytic dehydrogenative aromatization: an alternative route to functionalized arenes

Girard, Simon A.; Huang, Huawen; Zhou, Feng; Deng, Guo‐Jun; Li, Chao‐Jun

doi:10.1039/c4qo00358f

Cited by 105 publications

(48 citation statements)

References 34 publications

(32 reference statements)

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“…As previously discussed, our laboratory had already achieved the amine coupling and rearomatization of cyclohexanone and 2-cyclohexen-1-one, 95 as well as in the activation of phenol through hydrogen borrowing strategies. 95 While these procedures proved successful for anilines, 75,84 secondary amines, 77,85 primary alkyl amines, 83 and hydrazine; 96 it was not possible to perform the desired Nmodification on amino acids under these conditions. We presumed that this was due to the amino acid's inherent low nucleophilicity, pH sensitivity, and diverse functionalization at the α-position.…”

Section: R a F Tmentioning

confidence: 98%

Exploration of new reaction tools for late-stage functionalization of complex chemicals

et al. 2019

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Chemistry has always had as a target the conversion of molecules into valuable materials. Nevertheless, the aim of past synthesis has primarily focused on achieving a given transformation, regardless of the environmental impact of the synthetic route. Given the current global situation, the demand for sustainable alternatives has substantially increased. Our group focuses on developing selective chemical transformations that benefit from mild conditions, improved atom economy, and that can make use of renewable feedstocks as starting materials. This account summarizes our work over the past two decades specifically regarding the selective removal, conversion, and addition of functional groups that can, later on, be applied at a late stage for the modification of complex molecules.

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Section: R a F Tmentioning

confidence: 98%

Exploration of new reaction tools for late-stage functionalization of complex chemicals

et al. 2019

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“…The groups of Deng, Li and Lemaire have been particularly active in this area, as summarized in a recent account. 6 In this Perspective article, we present the concepts that guided our initial discovery of the cyclohexanone-to-phenol reaction, together with the subsequent development of related dehydrogenation reactions in our laboratory, including synthetic applications as well as mechanistic studies. This work is presented in in the context of work by of other groups, with the aim of providing relevant perspective on the utility of dehydrogenation reactions as synthetic methods.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products

2016

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Catalytic dehydrogenation of saturated or partially saturated six-membered carbocycles into aromatic rings represents an appealing strategy for the synthesis of substituted arenes. Particularly effective methods have been developed for the dehydrogenation of cyclohexanones and cyclohexenes into substituted phenol, aniline, and benzene derivatives, respectively. In this Perspective, we present the contributions of our research group to the discovery and development of palladium-based catalysts for aerobic oxidative dehydrogenation methods, including general methods for conversion of cyclohexanones and cyclohexenones into substituted phenols and a complementary method for partial dehydrogenation cyclohexanones to cyclohexenones. The mechanistic basis for chemoselective conversion of cyclohexanones to phenols or enones is presented. These results are presented within the context of recent methods developed by others for the synthesis of aryl ethers, anilines and other substituted arenes. Overall, Pd-catalyzed dehydrogenation methods provide a compelling strategy for selective synthesis of aromatic and related unsaturated molecules.

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“…In 2011, Stahl and co‐workers developed an efficient palladium‐catalyzed protocol to convert cyclohexanones into cyclohexenones or phenols under mild reaction conditions . Recently, we and others have developed various methods using cyclohexanones as the aryl source for the construction of C–C and C–heteroatom bonds as well as heterocyclic compounds in the presence or absence of transition metals . Based on our continuing interest in using cyclohexanones as aryl source for the construction of heterocyclic compounds under transition metal‐free conditions, herein, we disclose a novel route for the synthesis of substituted carbazoles from cyclohexnones and arylureas under transition metal‐free conditions.…”

Section: Methodsmentioning

confidence: 99%

Transition Metal‐Free Carbazole Synthesis from Arylureas and Cyclohexanones

Xie

Chen

et al. 2016

Adv Synth Catal

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An efficient strategy for carbazole synthesis from arylureasa nd cyclohexanones under transition metal-free conditions has been developed. The combined use of potassium iodide and iodine could significantly improve the reactione fficiency to provide 2,6-disubstituted9 -arylcarbazoles in moderate to good yields.I nt his kind of transformation,t he whole carbazole moiety (except the nitrogen atom) comes from two equivalents of cyclohexanones.

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Catalytic dehydrogenative aromatization: an alternative route to functionalized arenes

Abstract: Catalytic dehydrogenative aromatization has emerged as an efficient and environmentally friendly way to access functionalized arenes in recent years.

Cited by 105 publications

References 34 publications

Exploration of new reaction tools for late-stage functionalization of complex chemicals

Exploration of new reaction tools for late-stage functionalization of complex chemicals

Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products

Transition Metal‐Free Carbazole Synthesis from Arylureas and Cyclohexanones

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