Homogeneous Sc(OTf)3-Catalyzed Direct Allylation Reactions of General Alcohols with Allylsilanes

被引：9

作者：

Di, Yuanjun ^{[1
]}

Yoshimura, Tsutomu ^{[1
]}

Naito, Shun-ichi ^{[1
]}

Kimura, Yu ^{[2
]}

Kondo, Teruyuki ^{[1
]}

机构：

[1] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Grad Sch Engn, Nishikyo Ku, Kyoto 6158510, Japan

[2] Kyoto Univ, Ctr Promot Interdisciplinary Educ & Res, Nishikyo Ku, Kyoto 6158510, Japan

来源：

ACS OMEGA | 2018年 / 3卷 / 12期

关键词：

DIRECT COUPLING REACTION; BENZYLIC ALCOHOLS; B(C6F5)(3)-CATALYZED ALLYLATION; FACILE SYNTHESIS; IONIC LIQUIDS; LEWIS-ACID; LANTHANIDE; TRIFLATE; EFFICIENT; SILICON;

D O I：

10.1021/acsomega.8b01627

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Homogeneous Sc(OTf)(3) used in nitromethane showed excellent catalytic activity for the direct allylation reactions of general alcohols including benzylic, propargylic, allylic, and some aliphatic alcohols with allyltrimethylsilane under mild and neutral reaction conditions. Metal-free beta-silyl-substituted carbocations are intermediates generated by the highly oxophilic Sc(OTf)(3)-assisted rapid removal of a hydroxyl group in alcohols, which is supported by the result that allylation of (R)-1-(naphthalen-2-yl) ethan-1-ol with allytrimethylsilanes using the Sc(OTf)(3) catalyst combined with (R)- or (S)-[1,1'-binaphthalene]-2,2'-diol ligands gave only racemic 2-(pent-4-en-2-yl) naphthalene in quantitative yield. The present study resolves the argument about the uncertain catalytic activity of Sc(OTf)(3).

引用

页码：18885 / 18894

页数：10

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