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Efficient Protocol for Synthesis of ?-Hydroxy(alkoxy)selenides via Electrochemical Iodide-Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides.

ABSTRACT: An efficient protocol for the synthesis of ?-hydroxy(alkoxy)selenides was developed through the electrochemical iodide-catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides under mild reaction conditions. Mechanistic studies showed that the cation I⁺ is involved during the whole process, and accelerates the formation of seleniranium ion via substitution and addition reaction with dialkyl(aryl)diselenides and styrene derivatives. The corresponding products are formed in good to excellent yields. This electrochemical oxyselenation provides an efficient strategy for difunctionalization of alkenes.

SUBMITTER: Chen J

PROVIDER: S-EPMC6769433 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Efficient Protocol for Synthesis of β-Hydroxy(alkoxy)selenides via Electrochemical Iodide-Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides.

Chen Jinyang J Mei Lan L Wang Haiying H Hu Li L Sun Xiaorui X Shi Jianwei J Li Qiang Q

ChemistryOpen 20190910 10

An efficient protocol for the synthesis of β-hydroxy(alkoxy)selenides was developed through the electrochemical iodide-catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides under mild reaction conditions. Mechanistic studies showed that the cation I+ is involved during the whole process, and accelerates the formation of seleniranium ion via substitution and addition reaction with dialkyl(aryl)diselenides and styrene derivatives. The corresponding products are fo ...[more]

PMID: 31592067

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