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Issue 10, 2018
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Iodide reagent controlled reaction pathway of iodoperoxidation of alkenes: a high regioselectivity synthesis of α- and β-iodoperoxidates under solvent-free conditions

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Abstract

A highly atom economical, efficient and environmentally friendly iodoperoxidation of alkenes with tert-butyl hydroperoxide (TBHP) and iodide/iodine is reported in this paper. This method afforded a convenient path to obtain two different configurations of iodoperoxidates from the same starting materials. Notably, the regiodivergent iodoperoxidation reaction was achieved by using different iodide reagents. A series of control experiments were performed, which suggested the involvement of a radical pathway for the anti-Markovnikov type iodoperoxidates (α) in the combination of ammonium iodide (NH4I)/TBHP, and an active cationic iodine pathway for the Markovnikov type adduct (β) with iodine (I2) and TBHP.

Graphical abstract: Iodide reagent controlled reaction pathway of iodoperoxidation of alkenes: a high regioselectivity synthesis of α- and β-iodoperoxidates under solvent-free conditions

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Publication details

The article was received on 19 Jan 2018, accepted on 12 Apr 2018 and first published on 12 Apr 2018


Article type: Communication
DOI: 10.1039/C8GC00209F
Citation: Green Chem., 2018,20, 2225-2230
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    Iodide reagent controlled reaction pathway of iodoperoxidation of alkenes: a high regioselectivity synthesis of α- and β-iodoperoxidates under solvent-free conditions

    X. Gao, H. Yang, C. Cheng, Q. Jia, F. Gao, H. Chen, Q. Cai and C. Wang, Green Chem., 2018, 20, 2225
    DOI: 10.1039/C8GC00209F

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