Nucleophilic Bromodifluoromethylation of Iminium Ions

被引：59

作者：

Tsymbal, Artem V. ^{[1
,2
]}

Kosobokov, Mikhail D. ^{[1
]}

Levin, Vitalij V. ^{[1
]}

Struchkova, Marina I. ^{[1
]}

Dilman, Alexander D. ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia

[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 17期

基金：

俄罗斯科学基金会;

关键词：

CARBONYL-COMPOUNDS; LEWIS-ACID; ORGANOZINC REAGENTS; ADDITION-REACTION; RADICAL-ADDITION; TRIFLUOROMETHYLATION; DIFLUOROCARBENE; ALKYNES; SALTS; FLUOROALKYLATION;

D O I：

10.1021/jo501644m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for bromodifluoromethylation of iminium ions using Me3SiCF2Br is described. The reaction involves room temperature activation of the silicon reagent by HMPA to generate difluorocarbene, which upon interacting with excess of bromide ion provides bromodifluoromethyl carbanionic species. The iminium electrophiles are generated in situ from aldehydes, secondary amines, proton sponge, and silyl triflate. The reaction can be extended for introduction of chlorodifluoromethyl and iododifluoromethyl groups.

引用

页码：7831 / 7835

页数：5

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