Facile 1,1-Carboboration Reactions of Acetylenic Thioethers

被引：41

作者：

Eller, Christina ^{[1
]}

Kehr, Gerald ^{[1
]}

Daniliuc, Constantin G. ^{[1
]}

Froehlich, Roland ^{[1
]}

Erker, Gerhard ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ORGANOMETALLICS | 2013年 / 32卷 / 02期

关键词：

FRUSTRATED LEWIS PAIRS; ALKYNES; ROUTE; 1,1-ORGANOBORATION; DERIVATIVES; ACTIVATION;

D O I：

10.1021/om400016t

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The acetylenic thioether PhSC CSPh undergoes a rapid 1,1-carboboration reaction with facile -SPh migration upon treatment with B(C6F5)3 to yield the borylated ketene dithioacetal product (PhS)(2)C = C(C6F5)B(C6F5)(2) (8a). The X-ray crystal structure analysis revealed an intramolecular sulfur boron contact. The thioether PhC SPh undergoes an analogous 1,1-carboboration reaction with B(C6F5)(3). The resulting vicinal S/B frustrated Lewis pair undergoes 1,2-addition reactions to terminal acetylenes to give the respective zwitterionic six-membered heterocyclic sulfonium/borate products (all three examples were characterized by X-ray diffraction).

引用

页码：384 / 386

页数：3

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