The Nucleophilicity of Persistent -Monofluoromethide Anions

被引：17

作者：

Zhang, Zhe ^{[1
]}

Puente, Angel ^{[2
]}

Wang, Fang ^{[1
]}

Rahm, Martin ^{[1
,3
]}

Mei, Yuncai ^{[1
]}

Mayr, Herbert ^{[2
]}

Prakash, G. K. Surya ^{[1
]}

机构：

[1] Univ Southern Calif, Loker Hydrocarbon Res Inst, Dept Chem, Los Angeles, CA 90089 USA

[2] Univ Munich, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany

[3] Cornell Univ, Dept Chem & Chem Biol, Baker Lab, Ithaca, NY 14853 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 41期

关键词：

carbanions; fluorine effect; fluoromethylation; linear free energy relationship; nucleophilicity; ENANTIOSELECTIVE ORGANOCATALYTIC ADDITION; POLAR ORGANIC-REACTIVITY; PHASE S(N)2 REACTIONS; FLUORINATED SULFONES; ALPHA; BETA-UNSATURATED ALDEHYDES; ALLYLIC MONOFLUOROMETHYLATION; TRIFLUOROMETHANIDE ANION; FLUOROALKYLATION; CARBANIONS;

D O I：

10.1002/anie.201605616

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

-Fluorocarbanions are key intermediates in nucleophilic fluoroalkylation reactions. Although frequently discussed, the origin of the fluorine effect on the reactivity of -fluorinated CH acids has remained largely unexplored. We have now investigated the kinetics of a series of reactions of -substituted carbanions with reference electrophiles to elucidate the effects of -F, -Cl, and -OMe substituents on the nucleophilic reactivities of carbanions.

引用

页码：12845 / 12849

页数：5

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