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ATRA-like alkylation–peroxidation of alkenes with trichloromethyl derivatives by the combination of tBuOOH and NEt3

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Abstract

A method was developed for alkylation–peroxidation of alkenes using tert-butyl hydroperoxide (TBHP) and chloroform under metal-free conditions. This method is a unique and innovative approach to the construction of α-tert-butylperoxy-β-dichloromethyl alkanes, employing CHCl3 as an alkylating reagent to provide a –CHCl2 group, and TBHP as an oxidant to provide an α-tBuOO group. The reaction was successfully applied to carbon tetrachloride and 1,1,1-trichloroethane, and was regiospecific for terminal alkenes.

Graphical abstract: ATRA-like alkylation–peroxidation of alkenes with trichloromethyl derivatives by the combination of tBuOOH and NEt3

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Publication details

The article was received on 13 Aug 2018, accepted on 28 Sep 2018 and first published on 03 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00868J
Citation: Org. Chem. Front., 2018, Advance Article
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    ATRA-like alkylation–peroxidation of alkenes with trichloromethyl derivatives by the combination of tBuOOH and NEt3

    C. Chen, H. Tan, B. Liu, C. Yue and W. Liu, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00868J

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