Photoinduced Intermolecular Radical Hydroalkylation of Olefins via Ligated Boryl Radicals-Mediated Halogen Atom Transfer

被引：11
|
作者：
Wan, Ting [1 ,2 ]
Ciszewski, Lukasz W. [1 ,3 ]
Ravelli, Davide [4 ]
Capaldo, Luca [1 ,5 ]
机构：
[1] Univ Amsterdam, vant Hoff Inst Mol Sci HIMS, Flow Chem Grp, NL-1098 XH Amsterdam, Netherlands
[2] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Res Ctr Chiral Drugs, Shanghai 201203, Peoples R China
[3] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland
[4] Univ Pavia, Dept Chem, PhotoGreen Lab, I-27100 Pavia, Italy
[5] Univ Parma, SynCat Lab, Dept Chem Life Sci & Environm Sustainabil, I-43124 Parma, Italy
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 27期
关键词：
AMINOALKYL RADICALS; BORANE COMPLEXES; ALKYL-HALIDES; TRANSFER XAT; CATALYSIS; ACTIVATION; GENERATION; MERGER; TIN;
D O I：
10.1021/acs.orglett.4c02034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Light-mediated Halogen-Atom Transfer (XAT) has become a significant methodology in contemporary synthesis. Unlike alpha-aminoalkyl and silyl radicals, ligated boryl radicals (LBRs) have not been extensively explored as halogen atom abstractors. In this study, we introduce NHC-ligated boranes as optimal radical chain carriers for the intermolecular reductive radical hydroalkylation and hydroarylation of electron-deficient olefins by using direct UV-A light irradiation. DFT analysis allowed us to rationalize the critical role of the NHC ligand in facilitating efficient chain propagation.
引用
收藏
页码：5839 / 5843
页数：5
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