School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.
Angew Chem Int Ed Engl. 2017 Feb 6;56(7):1810-1814. doi: 10.1002/anie.201611058. Epub 2017 Jan 18.
In the presence of trifluoromethylsulfonium reagents, boronate complexes derived from 2-lithio furan and non-racemic secondary and tertiary alkyl or aryl boronic esters undergo deborylative three-component coupling to give the corresponding 2,5-disubstituted furans with excellent levels of enantiospecificity. The process proceeds via the reaction of boronate complexes with a trifluoromethyl radical, which triggers 1,2-metallate rearrangement upon single-electron oxidation. Alternative electrophiles can also be used in place of trifluoromethylsulfonium reagents to effect similar three-component coupling reactions.
在三氟甲基锍试剂的存在下，由 2-锂呋喃和非外消旋仲烷基或芳基硼酸酯衍生的硼酸酯配合物经历去硼化三组分偶联，以优异的对映选择性得到相应的 2,5-二取代呋喃。该过程通过硼酸酯配合物与三氟甲基自由基的反应进行，该反应在单电子氧化时引发 1,2-金属转移重排。也可以使用其他亲电试剂代替三氟甲基锍试剂来实现类似的三组分偶联反应。
