Metal-catalyzed C–H bond functionalization of phenol derivatives

Mamari, Hamad H. Al; Štefane, Bogdan; Žugelj, Helena Brodnik

doi:10.1016/j.tet.2020.130925

Cited by 28 publications

(14 citation statements)

References 76 publications

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“…Then we increased the pressure of CO to 20 bar, resulting in higher conversion but lower selectivity (Table , entries 5–7). As anticipated, ligands played a crucial role by controlling the product ratio (Table , entries 8–13). By adjusting the bite angle of the bisphosphine ligand, changing the ligand to 1,2-bis(diphenylphosphino)ethane (DPPE), a similar conversion (79%) but excellent selectivity of 2 (96:4) was obtained (Table , entry 10).…”

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confidence: 58%

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Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols

Zhang

Zhao

et al. 2020

Org. Lett.

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A rhodium-catalyzed carbonylative transformation of unactivated phenols to aryl salicylates is described. This protocol is characterized by utilizing 1,3-rhodium migration as the key step to provide direct access to synthesize o-hydroxyaryl esters. Various desired aryl o-hydroxybenzoates were produced in moderate to excellent yields with bis(dicyclohexylphosphino)ethane (DCPE) as the ligand. Interestingly, diphenyl carbonate was formed as the main product when 1,3-bis(diphenylphosphino)propane (DPPP) was used as the ligand. A plausible reaction mechanism is proposed.

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confidence: 58%

“…Based on the above results and previous reports, , a plausible mechanism is proposed (Scheme ). The reaction starts with ligand exchange of phenol to rhodium complex A .…”

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confidence: 59%

Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols

Zhang

Zhao

et al. 2020

Org. Lett.

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“…Thus catalysts based on various transition metals such as Pd, Rh, Ru, Ir, Au and Fe have allowed functionalization of inert C-H bonds in simple phenolic compounds and subsequently their transformation into new functionalized molecules. [33,34] Recently, 1,3-dipolar cycloaddition (Click chemistry) of cellulose-based azides with alkynes derived from phenolic compounds were transformed into new Phenolic Compounds: Classification, Chemistry, and Updated Techniques of Analysis… DOI: http://dx.doi.org/10.5772/intechopen.98958 phenolic compounds-based adducts (Figure 45). The new triazole products display some applicable anti UV properties.…”

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confidence: 99%

Phenolic Compounds: Classification, Chemistry, and Updated Techniques of Analysis and Synthesis

Mamari¹

2022

Biochemistry

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Phenolic compounds are vast, diverse, ubiquitous and widespread in nature. The biological significance of bioactive phenolic natural secondary metabolites is immense and of high and significant importance. Phenolic compounds are known to exhibit various biological activities such as antimicrobial, antioxidant and anti-inflammatory properties. This book chapter begins with classification of phenolic compounds in concise manner followed by going through their chemical properties that are essential for their biological activities. Some chemical properties such as acidity and formation of radicals are directly linked with their important and key biological activities such as antioxidant properties. The chapter covers methods and updated techniques of analysis of phenolic compounds. Finally, biosynthesis of such important organic molecules is covered going through some of their current synthesis methods in the laboratory, methods of their synthetic elaboration. Due to the high potential of phenolic compounds for applications in various industries such as pharmaceutical and food industries, the search for the development of efficient methods for their synthesis as well as modern and accurate methods for their detection and analysis will continue.

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“…Catalytic C-H bond activation and subsequent formation of new C-C bonds, or C-heteroatom bonds, have remarkably contributed to the development of chemical transformations which enable the construction of complex molecular architectures from readily available precursors by shortening synthetic pathways and reducing waste production [1][2][3][4][5][6][7]. Heteroarylation via C-H bond activation has been largely applied to material science, for example, the synthesis of conjugated dyes [8] and polymers [9].…”

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confidence: 99%

Conformationally Driven Ru(II)-Catalyzed Multiple ortho-C–H Bond Activation in Diphenylpyrazine Derivatives in Water: Where Is the Limit?

et al. 2020

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Ru(II)/carboxylate/PPh3 catalyst system enabled the preparation of highly conjugated pyrazine derivatives in water under microwave irradiation. Both nitrogen atoms efficiently dictated cleavage of the ortho-C–H bonds in both benzene rings of 2,3-diphenylpyrazine substrates through chelation assistance. In conformationally more flexible diphenyldihydropyrazine 1, the arylation of four ortho-C–H bonds was possible, while in the aromatic analog 2, the triarylation was the limit.

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Metal-catalyzed C–H bond functionalization of phenol derivatives

Cited by 28 publications

References 76 publications

Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols

Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols

Phenolic Compounds: Classification, Chemistry, and Updated Techniques of Analysis and Synthesis

Conformationally Driven Ru(II)-Catalyzed Multiple ortho-C–H Bond Activation in Diphenylpyrazine Derivatives in Water: Where Is the Limit?

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