Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corres...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 86; no. 17; pp. 12344 - 12353
Main Authors Yang, Yu-Ming, Yan, Wei, Hu, Han-Wei, Luo, Yimin, Tang, Zhen-Yu, Luo, Zhuangzhu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.09.2021
Amer Chemical Soc
Subjects
acetylation
Chemistry
Chemistry, Organic
cost effectiveness
diacetyl
light
organic chemistry
photosensitizing agents
Physical Sciences
Science & Technology
solvents
water solubility
ARYL DIAZONIUM
DIAZONIUM SALTS
ONE-POT
VISIBLE-LIGHT PHOTOREDOX
ORGANIC-REACTIONS
SELECTIVE HALOGENATION
DERIVATIVES
METAL-FREE
TRIFLUOROMETHYLATION
WATER
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.1c01290

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Summary:A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.1c01290