Chinese Journal of Organic Chemistry >
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)
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.
Yunshuai Huang , Xiaohui Jin , Fenglian Zhang , Yifeng Wang . 4-Dimethylaminopyridine-Boryl Radical Promoted Regioselective Radical Hydroboration of Electron-Deficient Alkenes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 1957 -1967 . DOI: 10.6023/cjoc202103041
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