Cu(I)- or Ag(I)-Catalyzed Regio- and Stereocontrolled trans-Hydrofluorination of Ynamides

Guangke He; Shineng Qiu; Hai Huang; Guohao Zhu; Dongming Zhang; Rong Zhang; Hongjun Zhu

doi:10.1021/acs.orglett.6b00615

Cu(I)- or Ag(I)-Catalyzed Regio- and Stereocontrolled trans-Hydrofluorination of Ynamides

Guangke He, Shineng Qiu, Hai Huang, Guohao Zhu, Dongming Zhang, Rong Zhang, Hongjun Zhu

School of Chemistry and Moleculai Engineering

Nanjing Tech University

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

56 Scopus citations

Abstract

With Et₃N·3HF as the fluorinating reagent, a copper(I)- or silver(I)-catalyzed β/α-site-regiocontrolled trans-hydrofluorination of alkynamides has been achieved, affording the corresponding fluoro enamides in moderate to nearly quantitative yields with high regio- and stereoselectivity, respectively. The reaction proceeds under mild reaction conditions and exhibits good functional group tolerance. Further, the deuterium-labeling experiment confirmed the existence of the alkenylcopper intermediate.

Original language	English
Pages (from-to)	1856-1859
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.6b00615
State	Published - 15 Apr 2016

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title = "Cu(I)- or Ag(I)-Catalyzed Regio- and Stereocontrolled trans-Hydrofluorination of Ynamides",

abstract = "With Et3N·3HF as the fluorinating reagent, a copper(I)- or silver(I)-catalyzed β/α-site-regiocontrolled trans-hydrofluorination of alkynamides has been achieved, affording the corresponding fluoro enamides in moderate to nearly quantitative yields with high regio- and stereoselectivity, respectively. The reaction proceeds under mild reaction conditions and exhibits good functional group tolerance. Further, the deuterium-labeling experiment confirmed the existence of the alkenylcopper intermediate.",

author = "Guangke He and Shineng Qiu and Hai Huang and Guohao Zhu and Dongming Zhang and Rong Zhang and Hongjun Zhu",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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doi = "10.1021/acs.orglett.6b00615",

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TY - JOUR

T1 - Cu(I)- or Ag(I)-Catalyzed Regio- and Stereocontrolled trans-Hydrofluorination of Ynamides

AU - He, Guangke

AU - Qiu, Shineng

AU - Huang, Hai

AU - Zhu, Guohao

AU - Zhang, Dongming

AU - Zhang, Rong

AU - Zhu, Hongjun

PY - 2016/4/15

Y1 - 2016/4/15

N2 - With Et3N·3HF as the fluorinating reagent, a copper(I)- or silver(I)-catalyzed β/α-site-regiocontrolled trans-hydrofluorination of alkynamides has been achieved, affording the corresponding fluoro enamides in moderate to nearly quantitative yields with high regio- and stereoselectivity, respectively. The reaction proceeds under mild reaction conditions and exhibits good functional group tolerance. Further, the deuterium-labeling experiment confirmed the existence of the alkenylcopper intermediate.

AB - With Et3N·3HF as the fluorinating reagent, a copper(I)- or silver(I)-catalyzed β/α-site-regiocontrolled trans-hydrofluorination of alkynamides has been achieved, affording the corresponding fluoro enamides in moderate to nearly quantitative yields with high regio- and stereoselectivity, respectively. The reaction proceeds under mild reaction conditions and exhibits good functional group tolerance. Further, the deuterium-labeling experiment confirmed the existence of the alkenylcopper intermediate.

UR - http://www.scopus.com/inward/record.url?scp=84966309532&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b00615

DO - 10.1021/acs.orglett.6b00615

M3 - 文章

AN - SCOPUS:84966309532

SN - 1523-7060

VL - 18

SP - 1856

EP - 1859

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Cu(I)- or Ag(I)-Catalyzed Regio- and Stereocontrolled trans-Hydrofluorination of Ynamides

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