Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 7693-7704 |
| Number of pages | 12 |
| Journal | ACS Omega |
| Volume | 5 |
| Issue number | 13 |
| DOIs | |
| State | Published - 7 Apr 2020 |
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In: ACS Omega, Vol. 5, No. 13, 07.04.2020, p. 7693-7704.
Research output: Contribution to journal › Article › peer-review
TY - JOUR
T1 - U.S. Food and Drug Administration-Certified Food Dyes as Organocatalysts in the Visible Light-Promoted Chlorination of Aromatics and Heteroaromatics
AU - Rogers, D.A.
AU - Hopkins, M.D.
AU - Rajagopal, N.
AU - Varshney, D.
AU - Howard, H.A.
AU - Leblanc, G.
AU - Lamar, A.A.
N1 - Cited By :3 Export Date: 14 June 2022 Correspondence Address: Leblanc, G.; Department of Chemistry and Biochemistry, United States; email: [email protected] Funding details: University of Tulsa, TU Funding details: Oklahoma Center for the Advancement of Science and Technology, OCAST, HR18-013 Funding text 1: The research results discussed in this publication were made possible in part by funding from the Oklahoma Center for the Advancement of Science and Technology (OCAST) Project Number HR18-013. In addition, we are grateful for financial support provided by The University of Tulsa (TU) lab start-up contribution, as well as the Tulsa Undergraduate Research Challenge (TURC) and Chemistry Summer Undergraduate Research Program (CSURP) for student support. References: Dalko, P.I., Moisan, L., In the golden age of organocatalysis (2004) Angew. Chem., Int. Ed., 43, pp. 5138-5175; Bertelsen, S., Jørgensen, K.A., Organocatalysis-After the gold rush (2009) Chem. Soc. 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PY - 2020/4/7
Y1 - 2020/4/7
N2 - 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.
AB - 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.
U2 - 10.1021/acsomega.0c00631
DO - 10.1021/acsomega.0c00631
M3 - Article
SN - 2470-1343
VL - 5
SP - 7693
EP - 7704
JO - ACS Omega
JF - ACS Omega
IS - 13
ER -