Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage

Muhammad Aliyu Idris; Kwang Ho Song; Sunwoo Lee

doi:10.1002/adsc.202200275

Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage

Muhammad Aliyu Idris, Kwang Ho Song, Sunwoo Lee

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

13 Citations (Scopus)

Abstract

Amides, such as N-benzoylsaccharin, N,N-diBocbenzamide, and N-phenyl-N-tosylbenzamides reacted with Et₃N⋅3HF to provide the corresponding acyl fluorides in good yields. The reaction was conducted under environmentally friendly conditions using i-PrOAc as the solvent. Moreover, the reaction was performed at room temperature and did not require a transition-metal catalyst or additives. The methodology showed functional group tolerance toward amines, alkoxy, halides, ketones, esters, and aldehydes. (Figure presented.).

Original language	English
Pages (from-to)	2449-2453
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	14
DOIs	https://doi.org/10.1002/adsc.202200275
Publication status	Published - 2022 Jul 19

Bibliographical note

Funding Information:
This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF-2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center.

Funding Information:
. This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF‐2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

C−N Bond Cleavage
N-benzoylsaccharin
acyl fluorides
amides
fluorides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.202200275

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title = "Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage",

abstract = "Amides, such as N-benzoylsaccharin, N,N-diBocbenzamide, and N-phenyl-N-tosylbenzamides reacted with Et3N⋅3HF to provide the corresponding acyl fluorides in good yields. The reaction was conducted under environmentally friendly conditions using i-PrOAc as the solvent. Moreover, the reaction was performed at room temperature and did not require a transition-metal catalyst or additives. The methodology showed functional group tolerance toward amines, alkoxy, halides, ketones, esters, and aldehydes. (Figure presented.).",

keywords = "C−N Bond Cleavage, N-benzoylsaccharin, acyl fluorides, amides, fluorides",

author = "{Aliyu Idris}, Muhammad and Song, {Kwang Ho} and Sunwoo Lee",

note = "Funding Information: This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF-2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center. Funding Information: . This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF‐2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = jul,

day = "19",

doi = "10.1002/adsc.202200275",

language = "English",

volume = "364",

pages = "2449--2453",

journal = "Advanced Synthesis and Catalysis",

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T1 - Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage

AU - Aliyu Idris, Muhammad

AU - Song, Kwang Ho

AU - Lee, Sunwoo

N1 - Funding Information: This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF-2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center. Funding Information: . This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF‐2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/7/19

Y1 - 2022/7/19

N2 - Amides, such as N-benzoylsaccharin, N,N-diBocbenzamide, and N-phenyl-N-tosylbenzamides reacted with Et3N⋅3HF to provide the corresponding acyl fluorides in good yields. The reaction was conducted under environmentally friendly conditions using i-PrOAc as the solvent. Moreover, the reaction was performed at room temperature and did not require a transition-metal catalyst or additives. The methodology showed functional group tolerance toward amines, alkoxy, halides, ketones, esters, and aldehydes. (Figure presented.).

AB - Amides, such as N-benzoylsaccharin, N,N-diBocbenzamide, and N-phenyl-N-tosylbenzamides reacted with Et3N⋅3HF to provide the corresponding acyl fluorides in good yields. The reaction was conducted under environmentally friendly conditions using i-PrOAc as the solvent. Moreover, the reaction was performed at room temperature and did not require a transition-metal catalyst or additives. The methodology showed functional group tolerance toward amines, alkoxy, halides, ketones, esters, and aldehydes. (Figure presented.).

KW - C−N Bond Cleavage

KW - N-benzoylsaccharin

KW - acyl fluorides

KW - amides

KW - fluorides

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U2 - 10.1002/adsc.202200275

DO - 10.1002/adsc.202200275

M3 - Article

AN - SCOPUS:85132322966

SN - 1615-4150

VL - 364

SP - 2449

EP - 2453

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 14

ER -

Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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