Synthesis of Arylated Nucleobases by Visible Light Photoredox Catalysis

J Org Chem. 2017 Apr 7;82(7):3552-3560. doi: 10.1021/acs.joc.7b00088. Epub 2017 Mar 10.

Abstract

Arylated nucleobases were synthesized by visible light photocatalysis using rhodamine 6G as photoredox catalyst and N,N-diisopropylethylamine as sacrificial electron donor. The high redox potential of this catalyst system is achieved by a consecutive photoinduced electron transfer process (conPET) and allows the room temperature conversion of brominated and chlorinated nucleobases or nucleobase precursors as starting materials. In contrast to many transition-metal-based syntheses, a direct C-H arylation of nitrogen-containing halogenated heterocycles is possible without protection of the N-H groups. The method provides a simple, metal-free alternative for the synthesis of biologically interesting arylated heterocycles under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't