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

D.A. Rogers, M.D. Hopkins, N. Rajagopal, D. Varshney, H.A. Howard, G. Leblanc, A.A. Lamar

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

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 N-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. Copyright © 2020 American Chemical Society.
Original languageEnglish
Pages (from-to)7693-7704
Number of pages12
JournalACS Omega
Volume5
Issue number13
DOIs
StatePublished - 7 Apr 2020

Fingerprint

Dive into the research topics of 'U.S. Food and Drug Administration-Certified Food Dyes as Organocatalysts in the Visible Light-Promoted Chlorination of Aromatics and Heteroaromatics'. Together they form a unique fingerprint.

Cite this