4-二甲胺基吡啶-硼自由基促进的缺电子烯烃区域选择性硼氢化反应
收稿日期: 2021-03-23
修回日期: 2021-04-09
网络出版日期: 2021-04-25
基金资助
国家自然科学基金(21971226); 中央高校基本科研业务费专项资金(WK2060000017)
4-Dimethylaminopyridine-Boryl Radical Promoted Regioselective Radical Hydroboration of Electron-Deficient Alkenes
Received date: 2021-03-23
Revised date: 2021-04-09
Online published: 2021-04-25
Supported by
National Natural Science Foundation of China(21971226); Fundamental Research Funds for the Central Universities(WK2060000017)
含硼有机化合物在合成化学中具有重要的应用价值, 硼氢化反应是构建有机硼化合物最常用的方法之一. 利用4-二甲氨基吡啶硼自由基与缺电子烯烃的自由基硼氢化反应, 高区域选择性地构建了α-硼取代产物. 该反应条件温和, 官能团容忍性好, 底物范围广. 多种α,β-不饱和酯、酰胺、羧酸、腈、三氟甲基化合物、砜以及磷酸酯均能顺利发生反应, 得到的含硼产物可以进一步应用于后续碳-碳键的构建.
关键词： 4-二甲氨基吡啶硼自由基; 缺电子烯烃; 区域选择性; 硼氢化反应; 自由基化学
黄云帅 , 靳小慧 , 张凤莲 , 汪义丰 . 4-二甲胺基吡啶-硼自由基促进的缺电子烯烃区域选择性硼氢化反应[J]. 有机化学, 2021 , 41(5) : 1957 -1967 . DOI: 10.6023/cjoc202103041
Organoboron compounds have shown significant applications in modern chemical synthesis. Hydroboration of alkenes is among the most widely used methods to access these targets. Herein, a regioselective radical hydroboration reaction of electron-deficient alkenes with 4-dimethylaminopyridine (DMAP)-boryl radical for the synthesis of α-boryl functionalized molecules is reported. The reaction features specific α-regioselectivity, mild reaction conditions, good functional group tolerance, and broad substrate scope. α,β-Unsaturated esters, amides, carboxylic acid, nitrile, trifluoromethyl molecule, sulfone, and phosphonate are viable substrates for this reaction. The resulting α-boryl functionalized molecules can be further transformed to various useful building blocks.
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