Photoinitiated stereoselective direct C(sp2)-H perfluoroalkylation and difluoroacetylation of enamides

Kai Zhao; Jing Yu Guo; Ting Guan; Ying Xue Wang; Ji Yu Tao; Yu Zhang; Qing Hong Zhang; Kun Ni; Teck Peng Loh

doi:10.1039/d1qo00605c

Photoinitiated stereoselective direct C(sp²)-H perfluoroalkylation and difluoroacetylation of enamides

Kai Zhao^*, Jing Yu Guo, Ting Guan, Ying Xue Wang, Ji Yu Tao, Yu Zhang, Qing Hong Zhang, Kun Ni, Teck Peng Loh^*

^*Corresponding author for this work

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

44 Citations (Scopus)

Abstract

A photoinitiated perfluoroalkylative coupling of enamides with perfluoroalkyl iodides and a visible-light-induced difluoroacetylation of enamides with ethyl bromodifluoroacetate have been developed, respectively. These transformations allow the efficacious and straightforward incorporation of biologically and physiologically privileged fluoro-containing moieties into synthetically eminent enamide scaffolds with excellent regio- and stereoselectivities under mild and environmentally friendly conditions.

Original language	English
Pages (from-to)	4086-4094
Number of pages	9
Journal	Organic Chemistry Frontiers
Volume	8
Issue number	15
DOIs	https://doi.org/10.1039/d1qo00605c
Publication status	Published - Aug 7 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© the Partner Organisations.

ASJC Scopus Subject Areas

Organic Chemistry

Access to Document

10.1039/d1qo00605c

Cite this

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title = "Photoinitiated stereoselective direct C(sp2)-H perfluoroalkylation and difluoroacetylation of enamides",

abstract = "A photoinitiated perfluoroalkylative coupling of enamides with perfluoroalkyl iodides and a visible-light-induced difluoroacetylation of enamides with ethyl bromodifluoroacetate have been developed, respectively. These transformations allow the efficacious and straightforward incorporation of biologically and physiologically privileged fluoro-containing moieties into synthetically eminent enamide scaffolds with excellent regio- and stereoselectivities under mild and environmentally friendly conditions.",

author = "Kai Zhao and Guo, \{Jing Yu\} and Ting Guan and Wang, \{Ying Xue\} and Tao, \{Ji Yu\} and Yu Zhang and Zhang, \{Qing Hong\} and Kun Ni and Loh, \{Teck Peng\}",

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doi = "10.1039/d1qo00605c",

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T1 - Photoinitiated stereoselective direct C(sp2)-H perfluoroalkylation and difluoroacetylation of enamides

AU - Zhao, Kai

AU - Guo, Jing Yu

AU - Guan, Ting

AU - Wang, Ying Xue

AU - Tao, Ji Yu

AU - Zhang, Yu

AU - Zhang, Qing Hong

AU - Ni, Kun

AU - Loh, Teck Peng

PY - 2021/8/7

Y1 - 2021/8/7

N2 - A photoinitiated perfluoroalkylative coupling of enamides with perfluoroalkyl iodides and a visible-light-induced difluoroacetylation of enamides with ethyl bromodifluoroacetate have been developed, respectively. These transformations allow the efficacious and straightforward incorporation of biologically and physiologically privileged fluoro-containing moieties into synthetically eminent enamide scaffolds with excellent regio- and stereoselectivities under mild and environmentally friendly conditions.

AB - A photoinitiated perfluoroalkylative coupling of enamides with perfluoroalkyl iodides and a visible-light-induced difluoroacetylation of enamides with ethyl bromodifluoroacetate have been developed, respectively. These transformations allow the efficacious and straightforward incorporation of biologically and physiologically privileged fluoro-containing moieties into synthetically eminent enamide scaffolds with excellent regio- and stereoselectivities under mild and environmentally friendly conditions.

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DO - 10.1039/d1qo00605c

M3 - Article

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VL - 8

SP - 4086

EP - 4094

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

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