Solvent-Promoted Catalyst-Free Nucleophilic Fluoroalkylation of Aldehydes

被引:7
|
作者
Komoda, Kazuki [1 ]
Shimokawa, Ai [1 ]
Amii, Hideki [1 ]
机构
[1] Gunma Univ, Div Mol Sci, Fac Sci & Technol, 1-5-1 Tenjin Cho, Kiryu, Gunma 3768515, Japan
来源
CHEMISTRYSELECT | 2019年 / 4卷 / 08期
基金
日本科学技术振兴机构;
关键词
fluorine; trifluoromethylation; fluoroalkylation; silicon; catalyst-free; solvent effect; CARBONYL-COMPOUNDS; ENANTIOSELECTIVE TRIFLUOROMETHYLATION; FACILE SYNTHESIS; ALPHA-TRIFLUOROMETHYL; IMINES; EFFICIENT; KETONES; DIFLUOROMETHYLATION; REAGENTS; PERFLUOROALKYLATION;
D O I
10.1002/slct.201900456
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Fluoroalkyl silanes are useful building blocks for nucleophilic introduction of fluoroalkyl groups into organic molecules. In general, fluoroalkyl silanes per se are stable compounds, but they are amenable to reactions as fluoroalkyl anion equivalents in the presence of base such as fluoride ion. Usually, KF acts as a good catalyst for nucleophilic fluoroalkylation of carbonyl compounds. To avoid the use of hygroscopic fluoride salts, we have developed a convenient catalyst-free method for nucleophilic fluoroalkylation of aldehydes and ketones by the use of fluoroalkyl silanes. Trifluoromethyl(trimethyl)silane (Me3Si-CF3), and other fluoroalkyl silanes (Me3Si-R-f) underwent solvent-promoted nucleophilic addition to aldehydes smoothly to give fluoroalkylated alcohols in good yields. In the present reactions, the use of polar solvents such as DMSO, DMF or NMP is essential to the formation of 1,2-adducts.
引用
收藏
页码:2374 / 2378
页数:5
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