(IPr)CuF-catalyzed α-site regiocontrolled: Trans -hydrofluorination of ynamides

Guohao Zhu; Shineng Qiu; Yang Xi; Yao Ding; Dongming Zhang; Rong Zhang; Guangke He; Hongjun Zhu

doi:10.1039/c6ob01345g

(IPr)CuF-catalyzed α-site regiocontrolled: Trans -hydrofluorination of ynamides

Guohao Zhu, Shineng Qiu, Yang Xi, Yao Ding, Dongming Zhang, Rong Zhang, Guangke He, Hongjun Zhu

School of Chemistry and Moleculai Engineering

Nanjing Tech University

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

28 Scopus citations

Abstract

With Et₃N·3HF as the fluorination reagent, (IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides has been achieved, affording (Z)-α-fluoroenamides in moderate to excellent yields. It was interesting to note that the regioselectivity of the reaction is reversed to that observed in the (Ph₃P)₃CuF-catalyzed hydrofluorination of ynamides. Additionally, a variety of different ynamides including oxazolidinonyl-, imidazolyl-, and N-sulfonyl ynamides were suitable for the reaction system and the subsequent oxidation of the fluorinated products enables a convenient synthesis to α-fluoroimides.

Original language	English
Pages (from-to)	7746-7753
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	32
DOIs	https://doi.org/10.1039/c6ob01345g
State	Published - 2016

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abstract = "With Et3N·3HF as the fluorination reagent, (IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides has been achieved, affording (Z)-α-fluoroenamides in moderate to excellent yields. It was interesting to note that the regioselectivity of the reaction is reversed to that observed in the (Ph3P)3CuF-catalyzed hydrofluorination of ynamides. Additionally, a variety of different ynamides including oxazolidinonyl-, imidazolyl-, and N-sulfonyl ynamides were suitable for the reaction system and the subsequent oxidation of the fluorinated products enables a convenient synthesis to α-fluoroimides.",

author = "Guohao Zhu and Shineng Qiu and Yang Xi and Yao Ding and Dongming Zhang and Rong Zhang and Guangke He and Hongjun Zhu",

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doi = "10.1039/c6ob01345g",

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TY - JOUR

T1 - (IPr)CuF-catalyzed α-site regiocontrolled

T2 - Trans -hydrofluorination of ynamides

AU - Zhu, Guohao

AU - Qiu, Shineng

AU - Xi, Yang

AU - Ding, Yao

AU - Zhang, Dongming

AU - Zhang, Rong

AU - He, Guangke

AU - Zhu, Hongjun

PY - 2016

Y1 - 2016

N2 - With Et3N·3HF as the fluorination reagent, (IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides has been achieved, affording (Z)-α-fluoroenamides in moderate to excellent yields. It was interesting to note that the regioselectivity of the reaction is reversed to that observed in the (Ph3P)3CuF-catalyzed hydrofluorination of ynamides. Additionally, a variety of different ynamides including oxazolidinonyl-, imidazolyl-, and N-sulfonyl ynamides were suitable for the reaction system and the subsequent oxidation of the fluorinated products enables a convenient synthesis to α-fluoroimides.

AB - With Et3N·3HF as the fluorination reagent, (IPr)CuF-catalyzed α-site regiocontrolled trans-hydrofluorination of ynamides has been achieved, affording (Z)-α-fluoroenamides in moderate to excellent yields. It was interesting to note that the regioselectivity of the reaction is reversed to that observed in the (Ph3P)3CuF-catalyzed hydrofluorination of ynamides. Additionally, a variety of different ynamides including oxazolidinonyl-, imidazolyl-, and N-sulfonyl ynamides were suitable for the reaction system and the subsequent oxidation of the fluorinated products enables a convenient synthesis to α-fluoroimides.

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DO - 10.1039/c6ob01345g

M3 - 文章

AN - SCOPUS:84982129597

SN - 1477-0520

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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ER -

(IPr)CuF-catalyzed α-site regiocontrolled: Trans -hydrofluorination of ynamides

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