Ambient-Light-Promoted Three-Component Annulation

Synthesis of Perfluoroalkylated Pyrimidines

Rui Wang, Wei Guan, Zheng Bo Han, Fushun Liang, Takeo Suga, Xihe Bi, Hiroyuki Nishide

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

An ambient-light-promoted and metal-free three-component reaction of active methylene compounds, perfluoroalkyl iodides, and guanidines/amidines is reported. This constitutes a powerful method to prepare perfluoroalkylated pyrimidines with mild reaction conditions, broad substrate scope, excellent functional group tolerance, and simple operation. A radical/polar mechanism involving the formation of a halogen-bond adduct and radical cross-coupling is proposed.

Original languageEnglish
Pages (from-to)2358-2361
Number of pages4
JournalOrganic Letters
Volume19
Issue number9
DOIs
Publication statusPublished - 2017 May 5

Fingerprint

Light Metals
Guanidines
Amidines
Pyrimidines
Halogens
Iodides
pyrimidines
Functional groups
Metals
guanidines
Light
cross coupling
Substrates
synthesis
methylene
halogens
iodides
adducts
metals

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ambient-Light-Promoted Three-Component Annulation : Synthesis of Perfluoroalkylated Pyrimidines. / Wang, Rui; Guan, Wei; Han, Zheng Bo; Liang, Fushun; Suga, Takeo; Bi, Xihe; Nishide, Hiroyuki.

In: Organic Letters, Vol. 19, No. 9, 05.05.2017, p. 2358-2361.

Research output: Contribution to journalArticle

Wang, Rui ; Guan, Wei ; Han, Zheng Bo ; Liang, Fushun ; Suga, Takeo ; Bi, Xihe ; Nishide, Hiroyuki. / Ambient-Light-Promoted Three-Component Annulation : Synthesis of Perfluoroalkylated Pyrimidines. In: Organic Letters. 2017 ; Vol. 19, No. 9. pp. 2358-2361.
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