Copper(II) mediated C–H methylthiolation of 2-phenyl pyridines with dimethyl sulfoxide using an amino acid ligand

Yan, Xiao; Wang, Shuo; Liu, Jian-Yu; Zhang, Hui; Xu, Yongnan

doi:10.1016/j.tetlet.2019.03.067

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Cu-catalyzed Methylthiolation1

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Cited by 10 publications

(2 citation statements)

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“…In recent years, Cu-mediated methylthiolation of heterocyclic compounds using DMSO as a simple, inexpensive, and easy-to-handle methylthiolation reagent was reported . Therefore, we explored the reaction of DMSO as the methylthiolation reagent and solvent with 6-methylthio-9-ethylpurine and obtained a low yield (35%) of 6a under our reaction conditions (Scheme ).…”

Section: Results and Discussionmentioning

confidence: 99%

Direct Sulfenylation of the Purine C₈–H Bond with Thiophenols

Jiang

Zhuge

et al. 2020

J. Org. Chem.

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The one-step copper-mediated regioselective formation of the C8–S bond for purine derivatives with arylthiols was achieved using air as the green oxidant in the presence of 1.0 equiv of Na2CO3 and stoichiometric CuCl and 1,10-phenanthroline monohydrate. This method provides an economical, easy-to-handle, and effective method for the synthesis of 8-sulfenylpurine derivatives in moderate to excellent yields. The reaction is selective for C8 over C2 and C6. It also tolerates a free amine on the purine, and it has a wide substrate scope.

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Section: Results and Discussionmentioning

confidence: 99%

Direct Sulfenylation of the Purine C₈–H Bond with Thiophenols

Jiang

Zhuge

et al. 2020

J. Org. Chem.

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“…Recently, great progress has been made in DMSO-mediated methylthiolation catalyzed by copper reagents. In 2019, Xu and Zhang's lab 92 established a C-H methylthiolation for synthesizing a series of aryl methyl sulfides 221 from 2-phenyl pyridines 220 using CuBr as the catalyst and DMSO as the sulfur source in the presence of an amino acid. This strategy has good substrate tolerance.…”

Section: Cu-catalyzed Methylthiolationmentioning

confidence: 99%