Methanesulfonic acid-catalyzed friedel-crafts alkylation: towards sustainable synthesis of arylalkanes from donor-acceptor cyclopropane ketones

TitleMethanesulfonic acid-catalyzed friedel-crafts alkylation: towards sustainable synthesis of arylalkanes from donor-acceptor cyclopropane ketones
Publication TypeJournal Article
Year of Publication2024
AuthorsGoswami, L, Paul, S, Mamale, AG, Gonnade, RG, Bhattacharya, AK
JournalAsian Journal of Organic Chemistry
Volume13
Issue7
Date PublishedJUL
Type of ArticleArticle
ISSN2193-5807
Keywordsdonor-acceptor cyclopropane, Friedel-Crafts alkylation, methanesulfonic acid, Phenols, thiophenol
Abstract

We present herein Br & oslash;nsted acid-catalyzed Friedel-Crafts alkylation of phenols with Donor-Acceptor cyclopropane ketones. The presence of the 1,4-diphenyl butan-1-one and 1,3-diphenyl propane-1-one motifs in various naturally occurring biologically significant molecules inspired us to pursue the direct synthesis of these structural frameworks. Utilizing methanesulfonic acid (MeSO3H) as a catalyst, we achieved a more environmentally friendly and high-yielding synthesis, owing to its cost-effectiveness, biodegradability, transition-metal and additives free conditions. Furthermore, we have successfully extended our developed methodology to thiophenols, resulting in the production of sulfur-based butan-1-one derivatives in good yields. The presence of 1,4-diphenyl butan-1-one and 1,3-diphenyl propane-1-one motifs in various naturally occurring biologically significant molecules prompted us to develop a Br & oslash;nsted acid-catalyzed Friedel-Crafts alkylation of phenols with Donor-Acceptor cyclopropane. image

DOI10.1002/ajoc.202400116
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.7

Divison category: 
Organic Chemistry
Physical and Materials Chemistry
Database: 
Web of Science (WoS)

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