Diethyl phosphite-mediated switchable synthesis of bis(imidazoheterocycles) derived disulfanes and sulfanes using imidazoheterocycles and octasulfur?
New Journal of Chemistry Pub Date: 2022-02-04 DOI: 10.1039/D1NJ05226H
Abstract
A practical and highly efficient oxidative dual C–H sulfenylation of imidazoheterocycles using odorless, inexpensive elemental sulfur in DMSO to synthesize sulfur-bridged imidazoheterocycles under metal-free conditions is reported. The amount of diethyl phosphite and sulfur powder most attractively permits a tunable synthesis of bis(imidazoheterocycle)disulfanes and bis(imidazoheterocycle)sulfanes in good to high yields. A comprehensive substrate scope with a broad range of functional group tolerance was realized, and the efficacy of the process was proved at gram-scale reactions. Next, the bis(imidazopyridine)disulfanes were smoothly reacted with various indoles under similar conditions to form the corresponding imidazo[1,2-a]pyridine-indole-derived thioethers in high yields. A plausible mechanism has been proposed based on the control experiments.
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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