Simple synthesized Mannich bases as ligands in Cu-catalyzed N-arylation of imidazoles in water

Zhu, Yefeng; Shi, Yixing; Wei, Yunyang

doi:10.1007/s00706-010-0363-8

Cited by 13 publications

(2 citation statements)

References 33 publications

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“…[20][21][22][23][24] Some Cu (I)-catalyzed CÀ N bond formation of imidazole, secondary amines, and different substituted aryl bromides have been developed, indicating good tolerance of other functional groups. [25][26][27][28][29] Additionally, a number of copper(I) complexes, [30,31] and copper(II) complexes [32][33][34][35][36] have been reported as pioneering contributions to the development of N-aryl bonds using amines/N(H)-heterocycles with admirable yields. Xiao et al [37] verified an alternate technique for Narylation of heterocyclic compounds using MCM-41-immobilized copper(I) complex under slight reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

“…Another prominent achievement was made for the N‐arylation of heterocyclic compounds via aryl halides using Cu 2 O as a heterogeneous catalyst [20–24] . Some Cu (I)‐catalyzed C−N bond formation of imidazole, secondary amines, and different substituted aryl bromides have been developed, indicating good tolerance of other functional groups [25–29] . Additionally, a number of copper(I) complexes, [30,31] and copper(II) complexes [32–36] have been reported as pioneering contributions to the development of N‐aryl bonds using amines/N(H)‐heterocycles with admirable yields.…”

Section: Introductionmentioning

confidence: 99%

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A Metal/Solvent/Additive Free Compliant Route to Ullmann‐Type C−N Coupling using Ionic Liquid Entangled Porphyrin Heterogeneous Photocatalyst

Barange

Bhagat

2022

ChemistrySelect

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N-Substituted pyrrole derivatives have been attracted as a prime source of biologically active compounds as therapeutic agents including antimicrobial, analgesic, and familiar antiproliferative agents in cancer treatment. Several metal-free reports have been documented for photocatalytic CÀ C/CÀ N bond formation to facilitate the synthesis of intermediates in pharmaceutical industries. In this protocol, we develop the scope of such methods, creating a green approach to achieve Ullmann-type CÀ N coupling. Particularly, we reveal a metal/ solvent/additive-free route, for the synthesis of N-substituted pyrroles using novel Brønsted acid-functionalized porphyrin grafted on 1,2,4-triazole-based ionic liquid (BAFPcTzIL) comprising donor-acceptor moiety. This new stable photocatalyst was confirmed by FT-IR, 1 HNMR, UV-Vis spectra to know Hammett acidity and energy bandgap by DR spectra. The optimized protocol was used significantly for reactions of morpholine, indole, pyrazole, imidazole, and benzimidazole with various inactivated aryl halides with good to excellent yields, under irradiations of 5 W LED in a homemade photocatalytic reactor. Moreover, the BAFPcTzIL could be readily separated by simple filtration and reused for 6 consecutive runs with admirable yield. The leaching test confirmed that porphyrin behaved like a perfect heterogeneous photocatalyst for CÀ N bond formation and might be attracted toward the synthesis of intermediates/ scaffolds in the pharma and fine chemical industry.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Metal/Solvent/Additive Free Compliant Route to Ullmann‐Type C−N Coupling using Ionic Liquid Entangled Porphyrin Heterogeneous Photocatalyst

Barange

Bhagat

2022

ChemistrySelect

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Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

2014

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The copper‐catalyzed arylation and vinylation of nitrogen nucleophiles is a highly versatile method for the construction of sp 2 C–N bonds. Copper‐catalyzed C–N bond formation has an extensive history and the field has been reinvigorated with the development of ligand‐promoted catalyst systems that provide general and effective reactions under relatively mild conditions. Copper promotes arylation and vinylation of a wide range of nitrogen nucleophiles, including amines, nitrogen heterocycles, and amide derivatives. The reactivity profile is complementary to that of palladium and often offers orthogonal chemoselectivity. This chapter presents a thorough overview of the copper‐catalyzed coupling of aryl and vinyl halides with nitrogen nucleophiles. Current understanding of the mechanism of this process is presented along with a detailed overview of the scope and limitations of this reaction along with optimal reaction conditions for the coupling of various nitrogen nucleophile classes.

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Iodine‐Catalyzed Selective Synthesis of 2‐Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides

Zhu

Wei

2013

Adv Synth Catal

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Iodine-catalyzed intermolecular dehydrogenative aromatizations of six-membered cyclohexanA C H T U N G T R E N N U N G ones for the selective synthesis of 2-sulfanylphenols have been developed. Both aryl and alkyl disulfides can be used as sulfanylation reagents to give the desired products in good yields under the optimized reaction conditions. The catalytic reaction uses dimethyl sulfoxide or oxygen as the terminal oxidant and avoids the use of transition metal catalysts. In addition, a-sulfanyl enones could also be obtained via an iodine-catalyzed oxidative system from simple cyclic ketones using dimethyl sulfoxide as the oxidant.

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Simple synthesized Mannich bases as ligands in Cu-catalyzed N-arylation of imidazoles in water

Cited by 13 publications

References 33 publications

A Metal/Solvent/Additive Free Compliant Route to Ullmann‐Type C−N Coupling using Ionic Liquid Entangled Porphyrin Heterogeneous Photocatalyst

A Metal/Solvent/Additive Free Compliant Route to Ullmann‐Type C−N Coupling using Ionic Liquid Entangled Porphyrin Heterogeneous Photocatalyst

Copper‐Catalyzed Amination of Aryl and Alkenyl Electrophiles

Iodine‐Catalyzed Selective Synthesis of 2‐Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides

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