Atom Transfer Radical Addition to Alkenes using Fukuzumi Photocatalyst for Regioselective Functionalization of Quinoxalin-2(1H)-ones

15 September 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The atom transfer radical addition (ATRA) reaction is defined as a method for introducing halogenated compounds into alkenes via a radical mechanism. In this study, we present an ATRA approach for achieving regioselective functionalization of quinoxalin-2(1H)-ones by activating C-Br bonds of CBr4, and subsequent trihaloalkyl-carbofunctionalization of styrenes employing the 9-mesityl-10-methylacridinium perchlorate (Fukuzumi) photocatalyst under 3W blue LED (450-470 nm) irradiation. This three-component radical cascade process demonstrates remarkable efficiency in the synthesis of 1-methyl-3-(3,3,3-tribromo-1-(4-chlorophenyl)propyl)quinoxalin-2(1H)-one derivatives.

Keywords

Atom Transfer Radical Addition (ATRA)
9-Mesityl-10-methylacridinium Perchlorate Photocatalyst
Visible light photocatalysis
Three Component Reaction (3-CR)
Quinoxalin-2(1H)-one

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