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Transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters†
Chemical Science ( IF 7.6 ) Pub Date : 2018-10-02 00:00:00 , DOI: 10.1039/c8sc03315c
Jin-Jiang Zhang 1, 2, 3, 4, 5 , Xin-Hua Duan 1, 2, 3, 4, 5 , Yong Wu 1, 2, 3, 4, 5 , Jun-Cheng Yang 1, 2, 3, 4, 5 , Li-Na Guo 1, 2, 3, 4, 5
Affiliation  

An efficient transition-metal free C–C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B2(OH)4 reagent not only served as the boron source but also acted as an electron donor source through formation of a complex with a DMAc-like Lewis base. This complex could be used as an efficient single electron reductant in other ring-opening transformations of cycloketone oxime esters. Free-radical trapping, radical-clock, and DFT calculations all suggest a radical pathway for this transformation.

中文翻译:

环酮肟酯的无​​过渡金属的C–C键裂解/碱化

已经描述了有效的无过渡金属的CC-C键裂解/环化酮肟酯的硼酸酯化反应。在该反应中,B 2(OH)4试剂不仅用作硼源,而且还通过与DMAc样的路易斯碱形成络合物而用作电子供体。该配合物可在环酮肟酯的其他开环转化中用作有效的单电子还原剂。自由基诱捕,激进时钟和DFT计算都为这种转变提供了一条激进的途径。
更新日期:2018-10-02
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