高价碘试剂通过光氧化还原催化实现硼选择性脱硼/脱羧烯基化反应。
Hypervalent iodine reagents enable chemoselective deboronative/decarboxylative alkenylation by photoredox catalysis.
机构信息
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
出版信息
Angew Chem Int Ed Engl. 2015 Feb 2;54(6):1881-4. doi: 10.1002/anie.201410176. Epub 2014 Dec 11.
Chemoselective C(sp(3))-C(sp(2)) coupling reactions under mild reaction conditions are useful for synthesizing alkyl-substituted alkenes having sensitive functional groups. Reported here is a visible-light-induced chemoselective alkenylation through a deboronation/decarboxylation sequence under neutral aqueous reaction conditions at room temperature. This reaction represents the first hypervalent-iodine-enabled radical decarboxylative alkenylation reaction, and a novel benziodoxole-vinyl carboxylic acid reaction intermediate was isolated. This C(sp(3))-C(sp(2)) coupling reaction leads to aryl-and acyl-substituted alkenes containing various sensitive functional groups. The excellent chemoselectivity, stable reactants, and neutral aqueous reaction conditions of the reaction suggest future biomolecule applications.
在温和的反应条件下，选择性的 C(sp(3))-C(sp(2)) 偶联反应对于合成具有敏感官能团的烷基取代的烯烃是有用的。这里报道的是一种可见光诱导的通过脱硼化/脱羧序列在中性水相反应条件下于室温下进行的选择性烯基化反应。该反应代表了第一个高价碘促进的自由基脱羧烯基化反应，并分离得到了一种新型苯并碘恶唑-乙烯基羧酸反应中间体。这种 C(sp(3))-C(sp(2)) 偶联反应得到了含有各种敏感官能团的芳基和酰基取代的烯烃。该反应具有优异的化学选择性、稳定的反应物和中性水相反应条件，这表明其在未来的生物分子应用中有很大的潜力。
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