Transition-Metal-Free Diboration Reaction by Activation of Diboron Compounds with Simple Lewis Bases

被引:243
作者
Bonet, Amadeu [2 ]
Pubill-Ulldemolins, Cristina [1 ,2 ]
Bo, Caries [1 ]
Gulyas, Henrik [2 ]
Fernandez, Elena [2 ]
机构
[1] ICIQ, Inst Chem Res Catalonia, Catalonia, Spain
[2] Univ Rovira & Virgili, Dept Quim Fis & Inorgan, Tarragona 43007, Spain
关键词
boron; density functional calculations; Lewis bases; organocatalysis; CATALYZED ENANTIOSELECTIVE DIBORATION; MOLECULAR-STRUCTURES; SIMPLE ALKENES; BORYL ANION; C-B; EFFICIENT; BORON; COMPLEXES; ADDUCTS; ALKYNES;
D O I
10.1002/anie.201101941
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Changing behavior: A nucleophilic sp2 carbene-type boryl moiety, formed upon interaction of tetraalkoxydiboranes and a Lewis base, can attack non-activated C=C bonds. Computational studies identify the interaction as the overlap between the strongly polarized B-B σ bond (HOMO) and the antibonding πorbital (LUMO) of the C=C bond. Conceptually, the normally electrophilic boron becomes nucleophilic and forces the olefin to act as an electrophile. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7158 / 7161
页数:4
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