Mild and efficient synthesis of -3-aryl-2-nitro-2,3-dihydrobenzofurans on water

An environmental-friendly and mild method has been successfully developed for the synthesis of 3-aryl-2-nitro-2,3-dihydrobenzofurans through domino Friedel-Crafts/substitution reaction of ( Z )-bromonitrostyrenes with sesamol. A variety of substrates performed well in this reaction, and the correspo...

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Bibliographic Details
Published in:New journal of chemistry 2020-07, Vol.44 (28), p.11937-1194
Main Authors: Feng, Juhua, Wang, Siyuan, Feng, Jinxiang, Li, Qiuju, Yue, Junping, Yue, Guizhou, Zou, Ping, Wang, Guangtu
Format: Article
Language:English
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Summary:An environmental-friendly and mild method has been successfully developed for the synthesis of 3-aryl-2-nitro-2,3-dihydrobenzofurans through domino Friedel-Crafts/substitution reaction of ( Z )-bromonitrostyrenes with sesamol. A variety of substrates performed well in this reaction, and the corresponding 3-aryl-2-nitro-2,3-dihydrobenzofurans were obtained in excellent yields (up to 99%). Significantly, water served as the sole green solvent. Remarkably, the crude products were purified by simple filtration, washing with water and drying in oven without any organic solvents or silica gel. A protocol to prepare trans -3-aryl-2-nitro-2,3-dihydrobenzofurans has been developed on water. The protocol avoids the use of toxic solvents, tedious work-up procedures, and chromatographic separation.
ISSN:1144-0546
1369-9261
DOI:10.1039/d0nj00548g