Transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters

被引：134
|
作者：
Zhang, Jin-Jiang [1 ]
Duan, Xin-Hua [1 ]
Wu, Yong [1 ]
Yang, Jun-Cheng [1 ]
Guo, Li-Na [1 ]
机构：
[1] Xi An Jiao Tong Univ, MOE Key Lab Nonequilibrium Synth & Modulat Conden, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
来源：
CHEMICAL SCIENCE | 2019年 / 10卷 / 01期
关键词：
CROSS-COUPLING REACTIONS; CYCLOBUTANONE O-BENZOYLOXIMES; COPPER-CATALYZED BORYLATION; ACID PROTEASOME INHIBITORS; B BOND; RING-CLEAVAGE; ARYL HALIDES; BIOLOGICAL EVALUATION; CONJUGATE ADDITIONS; MEDICINAL CHEMISTRY;
D O I：
10.1039/c8sc03315c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient transition-metal free C-C bond cleavage/borylation of cycloketone oxime esters has been described. In this reaction, the B-2(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.
引用
收藏
页码：161 / 166
页数：6
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