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美国食品药品监督管理局认证的食用色素作为可见光促进的芳烃和杂芳烃氯化反应中的有机催化剂。

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

作者信息

Rogers David A, Hopkins Megan D, Rajagopal Nitya, Varshney Dhruv, Howard Haley A, LeBlanc Gabriel, Lamar Angus A

机构信息

Department of Chemistry and Biochemistry, The University of Tulsa, 800 South Tucker Drive, Tulsa, Oklahoma 74104, United States.

出版信息

ACS Omega. 2020 Mar 24;5(13):7693-7704. doi: 10.1021/acsomega.0c00631. eCollection 2020 Apr 7.

DOI:10.1021/acsomega.0c00631
PMID:32280913
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7144131/
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.

摘要

七种获得美国食品药品监督管理局（FDA）认证的食用色素已作为有机催化剂进行了研究。结果发现，亮绿FCF和亮蓝FCF可作为多种芳烃和杂芳烃氯化反应的催化剂，产率适中至优异，区域选择性高。对各个体系的机理研究表明，存在不同的活化模式，亮绿FCF是一种光促进光氧化还原催化剂，可促进N-氯代琥珀酰亚胺（NCS）的单电子氧化，而亮蓝FCF以其磺酞形式作为氯转移催化剂，以1,3-二氯-5,5-二甲基海因（DCDMH）作为化学计量氯源。在一些实例中，使用亮蓝/DCDMH体系观察到萘酚和吲哚底物的脱芳构化反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/ddf9b1d22ba2/ao0c00631_0005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/ddf9b1d22ba2/ao0c00631_0005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/067221966836/ao0c00631_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/6aa71f36c68a/ao0c00631_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/dd382f1bbe60/ao0c00631_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/9a70d621346b/ao0c00631_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/1a184aa3ed32/ao0c00631_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ed76/7144131/ddf9b1d22ba2/ao0c00631_0005.jpg

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