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

David Philip Day; Jorge Andrés Mora Vargas; Antonio Carlos Bender Burtoloso

doi:10.1021/acs.joc.1c01441

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

David Philip Day, Jorge Andrés Mora Vargas, Antonio Carlos Bender Burtoloso (Lead / Corresponding author)

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17 Citations (Scopus)

Abstract

The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N3-, 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%.

Original language	English
Pages (from-to)	12427-12435
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	86
Issue number	17
Early online date	23 Aug 2021
DOIs	https://doi.org/10.1021/acs.joc.1c01441
Publication status	Published - 3 Sept 2021

Keywords

Azides
Hydrocarbons
Anions
Sodium
Ketones

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.1c01441

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

abstract = "The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N3-, 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%.",

keywords = "Azides, Hydrocarbons, Anions, Sodium, Ketones",

author = "Day, {David Philip} and {Mora Vargas}, {Jorge Andr{\'e}s} and Burtoloso, {Antonio Carlos Bender}",

note = "Funding Information: A.C.B.B. thanks FAPESP for financial support through grant no. 2020/07147-0. D.P.D. is grateful for funding and support through a FAPESP postdoctoral scholarship (2019/05002-8). We also wish to thank Prof. Dr. Antonio Gilberto Ferreira and Dr. Gabriela Carosio (Department of Chemistry, UFSCar) for acquiring NMR data. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

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doi = "10.1021/acs.joc.1c01441",

language = "English",

volume = "86",

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T1 - Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides

T2 - A One-Pot Approach

AU - Day, David Philip

AU - Mora Vargas, Jorge Andrés

AU - Burtoloso, Antonio Carlos Bender

N1 - Funding Information: A.C.B.B. thanks FAPESP for financial support through grant no. 2020/07147-0. D.P.D. is grateful for funding and support through a FAPESP postdoctoral scholarship (2019/05002-8). We also wish to thank Prof. Dr. Antonio Gilberto Ferreira and Dr. Gabriela Carosio (Department of Chemistry, UFSCar) for acquiring NMR data. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/9/3

Y1 - 2021/9/3

N2 - The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N3-, 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%.

AB - The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ and N3-, 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%.

KW - Azides

KW - Hydrocarbons

KW - Anions

KW - Sodium

KW - Ketones

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DO - 10.1021/acs.joc.1c01441

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AN - SCOPUS:85114451108

SN - 0022-3263

VL - 86

SP - 12427

EP - 12435

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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