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

38 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",

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

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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

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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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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