U.S. Food and Drug Administration-Certified Food Dyes As Organocatalysts in the Visible Light-Promoted Chlorination of Aromatics and Heteroaromatics

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Apr 14

PMID 32280913

Citations 3

Authors

David A Rogers

Megan D Hopkins

Nitya Rajagopal

Dhruv Varshney

Haley A Howard

Gabriel LeBlanc

Angus A Lamar

Affiliations

Soon will be listed here.

Abstract

Seven FDA-certified food dyes have been investigated as organocatalysts. As a result, Fast Green FCF and Brilliant Blue FCF have been discovered as catalysts for the chlorination of a wide range of arenes and heteroarenes in moderate to excellent yields and high regioselectivity. Mechanistic investigations of the separate systems indicate that different modes of activation are in operation, with Fast Green FCF being a light-promoted photoredox catalyst that is facilitating a one-electron oxidation of -chlorosuccinimide (NCS) and Brilliant Blue FCF serving as a chlorine-transfer catalyst in its sulfonphthalein form with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as stoichiometric chlorine source. Dearomatization of naphthol and indole substrates was observed in some examples using the Brilliant Blue/DCDMH system.

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