Combining Fluoroalkylation and Defluorination to Enable Formal [3 + 2 + 1] Heteroannulation by Using Visible-Light Photoredox Organocatalysis

Xue Qiang Chu; Ting Xie; Lin Li; Danhua Ge; Zhi Liang Shen; Teck Peng Loh

doi:10.1021/acs.orglett.8b00963

Combining Fluoroalkylation and Defluorination to Enable Formal [3 + 2 + 1] Heteroannulation by Using Visible-Light Photoredox Organocatalysis

Xue Qiang Chu, Ting Xie, Lin Li, Danhua Ge, Zhi Liang Shen, Teck Peng Loh

School of Chemistry and Moleculai Engineering

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

47 Scopus citations

Abstract

A metal-free, visible-light photoredox-catalyzed three-component [3 + 2 + 1] heteroannulation for accessing modular fluoroalkylated pyrimidines from readily available silyl enol ether, amidine, and fluoroalkyl halide is developed. This protocol distinguishes itself by broad functional group tolerance in a regioselective manner, which provides a complement to the existing methods for the construction of pharmaceutically and biologically active organofluorine compounds.

Original language	English
Pages (from-to)	2749-2752
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.8b00963
State	Published - 4 May 2018

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title = "Combining Fluoroalkylation and Defluorination to Enable Formal [3 + 2 + 1] Heteroannulation by Using Visible-Light Photoredox Organocatalysis",

abstract = "A metal-free, visible-light photoredox-catalyzed three-component [3 + 2 + 1] heteroannulation for accessing modular fluoroalkylated pyrimidines from readily available silyl enol ether, amidine, and fluoroalkyl halide is developed. This protocol distinguishes itself by broad functional group tolerance in a regioselective manner, which provides a complement to the existing methods for the construction of pharmaceutically and biologically active organofluorine compounds.",

author = "Chu, {Xue Qiang} and Ting Xie and Lin Li and Danhua Ge and Shen, {Zhi Liang} and Loh, {Teck Peng}",

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AU - Chu, Xue Qiang

AU - Xie, Ting

AU - Li, Lin

AU - Ge, Danhua

AU - Shen, Zhi Liang

AU - Loh, Teck Peng

PY - 2018/5/4

Y1 - 2018/5/4

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AB - A metal-free, visible-light photoredox-catalyzed three-component [3 + 2 + 1] heteroannulation for accessing modular fluoroalkylated pyrimidines from readily available silyl enol ether, amidine, and fluoroalkyl halide is developed. This protocol distinguishes itself by broad functional group tolerance in a regioselective manner, which provides a complement to the existing methods for the construction of pharmaceutically and biologically active organofluorine compounds.

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Combining Fluoroalkylation and Defluorination to Enable Formal [3 + 2 + 1] Heteroannulation by Using Visible-Light Photoredox Organocatalysis

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