Co(OAc)2-Catalyzed Trifluoromethylation and C(3)-Selective Arylation of 2-(Propargylamino)pyridines via a 6-Endo-Dig Cyclization

Jianjun Li; Yifan Lei; Yang Yu; Cong Qin; Yiwei Fu; Hao Li; Wei Wang

doi:10.1021/acs.orglett.7b02759

Co(OAc)₂-Catalyzed Trifluoromethylation and C(3)-Selective Arylation of 2-(Propargylamino)pyridines via a 6-Endo-Dig Cyclization

Jianjun Li, Yifan Lei, Yang Yu, Cong Qin, Yiwei Fu, Hao Li, Wei Wang

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

36 Scopus citations

Abstract

A Co(OAc)₂-catalyzed trifluoromethylation and subsequent C(3)-selective arylation of 2-(propargylamino)pyridines has been developed. A new 6-endo-dig cyclization involving an unprecedented C(3) selective arylation of the pyridines instead of a commonly observed 5-exo-dig cyclization with "N" is realized. Moreover, the study presents the first case of the installation of a trifluoromethyl group into electron-deficient azaarenes. The process delivers an efficient cascade approach to new trifluoromethylated 1,8-naphthyridine structures with a broad substrate scope.

Original language	English (US)
Pages (from-to)	6052-6055
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.7b02759
State	Published - Nov 17 2017
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Co(OAc)2-Catalyzed Trifluoromethylation and C(3)-Selective Arylation of 2-(Propargylamino)pyridines via a 6-Endo-Dig Cyclization",

abstract = "A Co(OAc)2-catalyzed trifluoromethylation and subsequent C(3)-selective arylation of 2-(propargylamino)pyridines has been developed. A new 6-endo-dig cyclization involving an unprecedented C(3) selective arylation of the pyridines instead of a commonly observed 5-exo-dig cyclization with {"}N{"} is realized. Moreover, the study presents the first case of the installation of a trifluoromethyl group into electron-deficient azaarenes. The process delivers an efficient cascade approach to new trifluoromethylated 1,8-naphthyridine structures with a broad substrate scope.",

author = "Jianjun Li and Yifan Lei and Yang Yu and Cong Qin and Yiwei Fu and Hao Li and Wei Wang",

note = "Funding Information: Financial support of this research from the program for the National Science Foundation of China (21738002, 21372073, 21572054, and 21572055), the Fundamental Research Funds for the Central Universities is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b02759",

language = "English (US)",

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T1 - Co(OAc)2-Catalyzed Trifluoromethylation and C(3)-Selective Arylation of 2-(Propargylamino)pyridines via a 6-Endo-Dig Cyclization

AU - Li, Jianjun

AU - Lei, Yifan

AU - Yu, Yang

AU - Qin, Cong

AU - Fu, Yiwei

AU - Li, Hao

AU - Wang, Wei

N1 - Funding Information: Financial support of this research from the program for the National Science Foundation of China (21738002, 21372073, 21572054, and 21572055), the Fundamental Research Funds for the Central Universities is gratefully acknowledged. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/11/17

Y1 - 2017/11/17

N2 - A Co(OAc)2-catalyzed trifluoromethylation and subsequent C(3)-selective arylation of 2-(propargylamino)pyridines has been developed. A new 6-endo-dig cyclization involving an unprecedented C(3) selective arylation of the pyridines instead of a commonly observed 5-exo-dig cyclization with "N" is realized. Moreover, the study presents the first case of the installation of a trifluoromethyl group into electron-deficient azaarenes. The process delivers an efficient cascade approach to new trifluoromethylated 1,8-naphthyridine structures with a broad substrate scope.

AB - A Co(OAc)2-catalyzed trifluoromethylation and subsequent C(3)-selective arylation of 2-(propargylamino)pyridines has been developed. A new 6-endo-dig cyclization involving an unprecedented C(3) selective arylation of the pyridines instead of a commonly observed 5-exo-dig cyclization with "N" is realized. Moreover, the study presents the first case of the installation of a trifluoromethyl group into electron-deficient azaarenes. The process delivers an efficient cascade approach to new trifluoromethylated 1,8-naphthyridine structures with a broad substrate scope.

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ER -

Co(OAc)₂-Catalyzed Trifluoromethylation and C(3)-Selective Arylation of 2-(Propargylamino)pyridines via a 6-Endo-Dig Cyclization

Abstract

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