A regioselective C7 bromination and C7 palladium-catalyzed Suzuki–Miyaura cross-coupling arylation of 4-substituted NH-free indazoles

Boujdi, Khalid; Brahmi, Nabil El; Graton, Jérôme; Dubreuil, Didier; Collet, Syl­vain; Mathé-Allainmat, Monique; Akssira, Mohamed; Lebreton, Jacques; Kazzouli, Saı̈d El

doi:10.1039/d0ra08598g

Cited by 7 publications

(3 citation statements)

References 64 publications

(68 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the other hand, cross-coupling reactions can join a wide range of organic molecules, including aryl halides, vinyl halides, aryl triflates, boronic acids or boronates, alkynes, and alkyl halides, to form a new molecule with a carbon–carbon bond. There are numerous publications, such as articles and reviews, that discuss C–H activation and cross-coupling reactions [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ]. These reactions have been extensively studied and widely used in organic synthesis, making them a popular research topic in chemistry.…”

Section: Introductionmentioning

confidence: 99%

Unlocking the Potential of Deep Eutectic Solvents for C–H Activation and Cross-Coupling Reactions: A Review

et al. 2023

Self Cite

View full text Add to dashboard Cite

Green chemistry principles have underpinned the development of deep eutectic solvents (DESs). In this brief overview, we discuss the potential of DESs as a greener alternative to volatile organic solvents for cross-coupling and C–H activation reactions in organic chemistry. DESs offer numerous benefits, such as easy preparation, low toxicity, high biodegradability, and the potential to replace volatile organic compounds. The ability of DESs to recover the catalyst-solvent system enhances their sustainability. This review highlights recent advances and challenges in utilizing DESs as a reaction media, as well as the impact of physicochemical properties on the reaction process. Several types of reactions are studied to highlight their effectiveness at promoting C–C bond formation. Aside from demonstrating the success of DESs in this context, this review also discusses the limitations and future prospects of DESs in organic chemistry.

show abstract

Section: Introductionmentioning

confidence: 99%

Unlocking the Potential of Deep Eutectic Solvents for C–H Activation and Cross-Coupling Reactions: A Review

et al. 2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…[6,7] Processes using transition metal catalysis have nowadays a privileged place in organic chemistry. For more than a century, the use of transition metals has made a major contribution to the field of organic synthesis, especially for the formation of carbon-carbon bonds, [8][9][10] permitting the development of cleaner synthesis processes compared to conventional methods that required the use of alkyl or aryl halides and organometallic derivatives (examples: Suzuki-Miyaura, [11] Heck, [12] Sonogashira, [13] Stille [14] and Negish [15] cross-couplings).…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Site‐Selective C7 Oxidative Arylation of 4‐EWG‐1H‐Indazoles

Ouazzani Chahdi,

Boujdi,

El Brahmi

et al. 2023

Asian J Org Chem

Self Cite

View full text Add to dashboard Cite

An efficient palladium‐catalyzed oxidative arylation of substituted 1H‐indazole with various arenes and heteroarenes as coupling partners is reported. A site selective C7 oxidative arylation was perfectly achieved with a directing electron‐withdrawing groups (EWG) located at the C4 position of the 1H‐indazole. The desired products are obtained in moderate to good yields from 4‐NO2 or 4‐CO2Me 1H‐indazoles and various (hetero)aryls as coupling partners in the presence of Pd(OAc)2 as catalyst, phenanthroline as ligand, Ag2CO3 as oxidant and NaOH as the base. Density functional theory was also conducted for reaction mechanism comprehension. This approach provides a highly effective, direct, and atom economical way to build C7‐ (het)arylated 1H‐indazole compounds.

show abstract

“…However, the application of indazoles in optoelectronic materials is still limited since only a few studies have reported synthetic pathways for the extension of the π‐conjugated system of indazoles [6] . In particular, the number of studies on N ‐unsubstituted 1 H ‐indazole derivatives is even more limited [6k,l] . Phosphorescent materials are one of the most promising organic optoelectronic materials that are applied in the fabrication of sensors and organic electroluminescent materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐(Phenylcarbonyl)‐1H‐indazole Derivatives through Intramolecular Cyclization under Mild Conditions

et al. 2022

View full text Add to dashboard Cite

The synthesis of 3‐(phenylcarbonyl)‐1H‐indazole derivatives via the intramolecular cyclization of triazene derivatives substituted by a 2‐(phenylethynyl)phenyl group at the position 3 was developed. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide (TMSI) obtained from an in situ mixture of trimethylsilyl chloride (TMSCl) and sodium iodide (NaI). The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence, which was verified by theoretical calculations.

show abstract

A regioselective C7 bromination and C7 palladium-catalyzed Suzuki–Miyaura cross-coupling arylation of 4-substituted NH-free indazoles

Abstract: A regioselective C7-bromination of 4-substituted 1H-indazoles followed by a palladium-catalyzed Suzuki–Miyaura reaction with boronic acids is described.

Cited by 7 publications

References 64 publications

Unlocking the Potential of Deep Eutectic Solvents for C–H Activation and Cross-Coupling Reactions: A Review

Unlocking the Potential of Deep Eutectic Solvents for C–H Activation and Cross-Coupling Reactions: A Review

Palladium‐Catalyzed Site‐Selective C7 Oxidative Arylation of 4‐EWG‐1H‐Indazoles

Synthesis of 3‐(Phenylcarbonyl)‐1H‐indazole Derivatives through Intramolecular Cyclization under Mild Conditions

Contact Info

Product

Resources

About