Methanesulfonic acid-catalyzed friedel-crafts alkylation: towards sustainable synthesis of arylalkanes from donor-acceptor cyclopropane ketones
Title | Methanesulfonic acid-catalyzed friedel-crafts alkylation: towards sustainable synthesis of arylalkanes from donor-acceptor cyclopropane ketones |
Publication Type | Journal Article |
Year of Publication | 2024 |
Authors | Goswami, L, Paul, S, Mamale, AG, Gonnade, RG, Bhattacharya, AK |
Journal | Asian Journal of Organic Chemistry |
Volume | 13 |
Issue | 7 |
Date Published | JUL |
Type of Article | Article |
ISSN | 2193-5807 |
Keywords | donor-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 |
DOI | 10.1002/ajoc.202400116 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 2.7 |
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