Palladium-Catalyzed Regioselective C3-Allylic Alkylation of 2-Aryl Imidazopyridines with MBH Carbonates

Murugesan, Tamilarasu; Elikkottil, Afna; Alagiri, Kaliyamoorthy

doi:10.1021/acs.joc.2c03001

Cited by 7 publications

(3 citation statements)

References 75 publications

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“…X-ray crystallography analysis was performed on a Bruker D8 Venture X-ray diffractometer. All of the MBH carbonates and N -(2- tert -butylphenyl)maleimides in this paper are known compounds and were prepared according to the reported literature. Catalysts rac-C and C1 – C7 were synthesized by our laboratory …”

Section: Methodsmentioning

confidence: 99%

Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides

Hou,

Hao,

Chen

et al. 2024

J. Org. Chem.

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Herein, we report an l-valine-derived amide phosphine-catalyzed [3+2] cyclization of MBH carbonates and N-(2-tert-butylphenyl)maleimides via asymmetric desymmetrization. Bicyclic N-aryl succinimide derivatives bearing three continuous chiral centers with a remote C–N atropisomeric chirality were constructed stereospecifically and enantioselectively. A wide variety of MBH carbonates could be employed in this process to deliver highly optically pure succinimide derivatives in moderate to excellent yields.

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Section: Methodsmentioning

confidence: 99%

Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides

Hou,

Hao,

Chen

et al. 2024

J. Org. Chem.

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“…Direct C–H functionalization of imidazoheterocycles has attracted the attention of synthetic chemists due to the importance of functionalized imidazoheterocycles in the field of pharmaceuticals, materials science, and organometallics. , Despite the significant progress in this area, only one report is available in the literature for the direct C-3 C–H allylic alkylation of imidazoheterocycles employing MBH carbonates via palladium catalysis . Few reports are available for direct C–H iodination of imidazoheterocycles employing iodine as an iodinating agent in the presence of either a catalytic zwitterionic salt or stoichiometric amount of tert -butyl hydroperoxide (TBHP) as oxidant under sonication .…”

Section: Introductionmentioning

confidence: 99%

Tunable Regioselective Allylic Alkylation/Iodination of Imidazoheterocycles in Water

Paul,

Choudhuri,

Das

et al. 2024

J. Org. Chem.

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The switchable roles of allylic alcohol and molecular iodine as reagents and catalysts have been demonstrated in the regioselective allylic alkylation and iodination of imidazoheterocycles employing the mixture of allylic alcohol-I 2 . First, we have explored the catalytic activity of iodine for the allylation of imidazoheterocycles using allylic alcohol in an aqueous medium. The allylation of a library of imidazoheterocycles and other electron-rich heterocycles like indole, pyrazole, 4-hydroxy coumarin, and 6-amino uracil has been achieved by employing this methodology. The efficiency of the I 2 catalyst for N-allylation of azoles has also been demonstrated. Next, we have shown that this mixture of allylic alcohol and I 2 could be beneficial for the iodination of imidazoheterocycles under room temperature. Mechanistic studies indicate that the activation of allylic alcohol by molecular iodine took place probably through halogen bonding, and NMR studies show that the reaction did not proceed through allylic ether formation.

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“…Then, intermediate (II) was trapped by N- tosylhydrazones to give intermediate (III) . Finally, intermediate (III) underwent a deprotonation process to afford product 3a with the regeneration of the catalyst Pd(0) species in the catalytic cycle …”

mentioning

confidence: 99%

Chemodivergent Synthesis of Sulfonamide and Sulfones from N-Tosylhydrazones by Switching Catalyst and Temperature

Jin

Wang

et al. 2023

Org. Lett.

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A catalyst- and temperature-controlled selective synthesis of sulfonamide and sulfones from N-tosylhydrazones and MBH carbonates has been developed. The use of palladium catalysts exclusively leads to sulfonamide products at room temperature, whereas the selective synthesis of sulfones is dominant for a temperature-controlled coupling reaction without palladium catalysis. Importantly, the catalyst- or temperature-controlled reaction exhibits high nucleophilicity rather than carbene reactivity in these transformations.

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Palladium-Catalyzed Regioselective C3-Allylic Alkylation of 2-Aryl Imidazopyridines with MBH Carbonates

Cited by 7 publications

References 75 publications

Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides

Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides

Tunable Regioselective Allylic Alkylation/Iodination of Imidazoheterocycles in Water

Chemodivergent Synthesis of Sulfonamide and Sulfones from N-Tosylhydrazones by Switching Catalyst and Temperature

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