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Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes.

ABSTRACT: We developed a direct vicinal difunctionalization of alkenes with iodine and TBHP at room temperature. This iodination and peroxidation in a one-pot synthesis produces 1-(tert-butylperoxy)-2-iodoethanes, which are inaccessible through conventional synthetic methods. This method generates multiple radical intermediates in situ and has excellent regioselectivity, a broad substrate scope and mild conditions. The iodine and peroxide groups of 1-(tert-butylperoxy)-2-iodoethanes have several potential applications and allow further chemical modifications, enabling the preparation of synthetically valuable molecules.

SUBMITTER: Wang H 

PROVIDER: S-EPMC5629392 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Difunctionalization of alkenes with iodine and <i>tert</i>-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(<i>tert</i>-butylperoxy)-2-iodoethanes.

Wang Hao H   Chen Cui C   Liu Weibing W   Zhu Zhibo Z  

Beilstein journal of organic chemistry 20170928

We developed a direct vicinal difunctionalization of alkenes with iodine and TBHP at room temperature. This iodination and peroxidation in a one-pot synthesis produces 1-(<i>tert</i>-butylperoxy)-2-iodoethanes, which are inaccessible through conventional synthetic methods. This method generates multiple radical intermediates in situ and has excellent regioselectivity, a broad substrate scope and mild conditions. The iodine and peroxide groups of 1-(<i>tert</i>-butylperoxy)-2-iodoethanes have sev  ...[more]

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