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

页码：12427 / 12435

页数：9

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