Ring-Opening Fluorination of Isoxazoles

Masaaki Komatsuda; Hugo Ohki; Hiroki Kondo; Ayane Suto; Junichiro Yamaguchi

doi:10.1021/acs.orglett.2c01149

Ring-Opening Fluorination of Isoxazoles

Masaaki Komatsuda, Hugo Ohki, Hiroki Kondo, Ayane Suto, Junichiro Yamaguchi^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

A ring-opening fluorination of isoxazoles has been developed. Upon treatment of isoxazoles with an electrophilic fluorinating agent (Selectfluor), fluorination followed by deprotonation leads to tertiary fluorinated carbonyl compounds. This method features mild reaction conditions, good functional group tolerance, and a simple experimental procedure. Diverse transformations of the resulting α-fluorocyanoketones were also demonstrated, furnishing a variety of fluorinated compounds.

Original language	English
Pages (from-to)	3270-3274
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.2c01149
Publication status	Published - 2022 May 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c01149

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title = "Ring-Opening Fluorination of Isoxazoles",

abstract = "A ring-opening fluorination of isoxazoles has been developed. Upon treatment of isoxazoles with an electrophilic fluorinating agent (Selectfluor), fluorination followed by deprotonation leads to tertiary fluorinated carbonyl compounds. This method features mild reaction conditions, good functional group tolerance, and a simple experimental procedure. Diverse transformations of the resulting α-fluorocyanoketones were also demonstrated, furnishing a variety of fluorinated compounds.",

author = "Masaaki Komatsuda and Hugo Ohki and Hiroki Kondo and Ayane Suto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grants JP19H02726, JP21H05213, and JP21K18966 (to J.Y.) and Grant JP20J14905 and a Waseda Research Institute for Science and Engineering Grant in Aid for Young Scientists (Early Bird) (to M.K.). The authors thank Dr. Kenta Kato (Waseda University) for assistance with X-ray crystallographic analysis. The Materials Characterization Central Laboratory of Waseda University is acknowledged for the support of HRMS measurement. Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

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doi = "10.1021/acs.orglett.2c01149",

language = "English",

volume = "24",

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journal = "Organic Letters",

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T1 - Ring-Opening Fluorination of Isoxazoles

AU - Komatsuda, Masaaki

AU - Ohki, Hugo

AU - Kondo, Hiroki

AU - Suto, Ayane

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grants JP19H02726, JP21H05213, and JP21K18966 (to J.Y.) and Grant JP20J14905 and a Waseda Research Institute for Science and Engineering Grant in Aid for Young Scientists (Early Bird) (to M.K.). The authors thank Dr. Kenta Kato (Waseda University) for assistance with X-ray crystallographic analysis. The Materials Characterization Central Laboratory of Waseda University is acknowledged for the support of HRMS measurement. Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/5/6

Y1 - 2022/5/6

N2 - A ring-opening fluorination of isoxazoles has been developed. Upon treatment of isoxazoles with an electrophilic fluorinating agent (Selectfluor), fluorination followed by deprotonation leads to tertiary fluorinated carbonyl compounds. This method features mild reaction conditions, good functional group tolerance, and a simple experimental procedure. Diverse transformations of the resulting α-fluorocyanoketones were also demonstrated, furnishing a variety of fluorinated compounds.

AB - A ring-opening fluorination of isoxazoles has been developed. Upon treatment of isoxazoles with an electrophilic fluorinating agent (Selectfluor), fluorination followed by deprotonation leads to tertiary fluorinated carbonyl compounds. This method features mild reaction conditions, good functional group tolerance, and a simple experimental procedure. Diverse transformations of the resulting α-fluorocyanoketones were also demonstrated, furnishing a variety of fluorinated compounds.

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JO - Organic Letters

JF - Organic Letters

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Ring-Opening Fluorination of Isoxazoles

Abstract

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