Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach

被引：20
作者：
Day, David Philip [1 ]
Mora Vargas, Jorge Andres [1 ]
Bender Burtoloso, Antonio Carlos [1 ]
机构：
[1] Univ Sao Paulo, Sao Carlos Inst Chem, BR-13560970 Sao Carlos, SP, Brazil
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 17期
基金：
巴西圣保罗研究基金会;
关键词：
ALPHA-AZIDO KETONES; DRUG DESIGN; ALKYNE; CLICK; FLUORINATION; CHEMISTRY; 1,2,3-TRIAZOLES; CYCLOADDITION; FLUOROKETONES; AZIDOKETONES;
D O I：
10.1021/acs.joc.1c01441
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The work reported herein showcases a new route to access alpha-fluoro-alpha-triazol-1-yl ketones from sulfoxonium ylides via aazido-alpha-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N-3(-), followed by a subsequent CuAAC reaction with arylacetylenes to install a 1,4-triazolo moiety. The approach allows for modification to both the sulfoxonium ylide and arylacetylene reactants. Fifteen examples have been reported, with yields ranging between 22% and 75%.
引用
收藏
页码：12427 / 12435
页数：9
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