Copper-catalyzed three-component reaction for the synthesis of fluoroalkoxyl imidates

A Cu-catalyzed three-component reaction of aromatic terminal alkynes with aryl sulfonyl azides and primary fluoroalkyl alcohols for the synthesis of fluoroalkoxyl imidates was developed. This simple method enabled the efficient synthesis of trifluoroethoxyl, pentafluoropropoxyl, and heptafluorobutox...

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Bibliographic Details
Published inTetrahedron Vol. 74; no. 46; pp. 6631 - 6634
Main Authors Wang, Zeng, Ding, Xinzhi, Li, Shiwei, Weng, Zhiqiang
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.11.2018
Elsevier
Subjects
Chemistry
Chemistry, Organic
Copper
Heptafluorobutoxylation
Imidates
Pentafluoropropoxylation
Physical Sciences
Science & Technology
Three-component reaction
Trifluoroethoxylation
Imidates
Pentafluoropropoxylation
Three-component reaction
Copper
Trifluoroethoxylation
Heptafluorobutoxylation
2,2,2-TRIFLUOROETHOXYLATION
TERMINAL ALKYNES
BROMIDES
KETONES
ETHERS
SULFONYL AZIDES
C-H TRIFLUOROETHOXYLATION
ARYL
EFFICIENT
AMIDES
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Summary:A Cu-catalyzed three-component reaction of aromatic terminal alkynes with aryl sulfonyl azides and primary fluoroalkyl alcohols for the synthesis of fluoroalkoxyl imidates was developed. This simple method enabled the efficient synthesis of trifluoroethoxyl, pentafluoropropoxyl, and heptafluorobutoxyl imidates in good to excellent yields under mild reaction conditions with excellent functional group tolerance. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.09.056