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

• DOI: 10.3762/bjoc.13.200
• Publication Date: 2017-09-28T09:43:00Z
• Authors: Hao Wang; Cui Chen; Weibing Liu; Zhibo Zhu
• Keywords: QD241-441; Letter; Science; TBHP; Q; Organic chemistry; difunctionalization of alkenesiodine; iodination–peroxidation reaction; 01 natural sciences; 0104 chemical sciences

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.