Methanesulfonic Acid‐Catalyzed Friedel‐Crafts Alkylation: Towards Sustainable Synthesis of Arylalkanes from Donor–Acceptor Cyclopropane Ketones
We present herein Brønsted 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 dire...
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creator | Goswami, Lakshmi Paul, Sayantan Mamale, Ajay G. Gonnade, Rajesh G. Bhattacharya, Asish K. |
description | We present herein Brønsted 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 Brønsted acid‐catalyzed Friedel‐Crafts alkylation of phenols with Donor–Acceptor cyclopropane. |
doi_str_mv | 10.1002/ajoc.202400116 |
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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 Brønsted acid‐catalyzed Friedel‐Crafts alkylation of phenols with Donor–Acceptor cyclopropane.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202400116</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkylation ; Chemical synthesis ; Cyclopropane ; donor–acceptor cyclopropane ; Friedel-Crafts alkylation ; Ketones ; Methanesulfonic acid ; Phenols ; thiophenol</subject><ispartof>Asian journal of organic chemistry, 2024-07, Vol.13 (7), p.n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2726-480b8c5d3521869e5c99084c47101cefb0be8472ebdf32f8e3dedf00784fbc7f3</cites><orcidid>0009-0009-1717-2179 ; 0000-0003-4331-394X ; 0000-0001-7731-9237 ; 0000-0002-2841-0197 ; 0000-0002-9162-522X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fajoc.202400116$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202400116$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Goswami, Lakshmi</creatorcontrib><creatorcontrib>Paul, Sayantan</creatorcontrib><creatorcontrib>Mamale, Ajay G.</creatorcontrib><creatorcontrib>Gonnade, Rajesh G.</creatorcontrib><creatorcontrib>Bhattacharya, Asish K.</creatorcontrib><title>Methanesulfonic Acid‐Catalyzed Friedel‐Crafts Alkylation: Towards Sustainable Synthesis of Arylalkanes from Donor–Acceptor Cyclopropane Ketones</title><title>Asian journal of organic chemistry</title><description>We present herein Brønsted 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 Brønsted acid‐catalyzed Friedel‐Crafts alkylation of phenols with Donor–Acceptor cyclopropane.</description><subject>Alkylation</subject><subject>Chemical synthesis</subject><subject>Cyclopropane</subject><subject>donor–acceptor cyclopropane</subject><subject>Friedel-Crafts alkylation</subject><subject>Ketones</subject><subject>Methanesulfonic acid</subject><subject>Phenols</subject><subject>thiophenol</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkMtOwzAQRSMEEqh0y9oS6xTbSWqHXRTeD3VRWEeOMxYpJi62qyqs-glIiB_kS3BUBEtmM6PRuXM1N4qOCJ4QjOmJWBg5oZimGBMy3YkOKMmTOOMk2_2dMduPxs4tcCjGckLzg-jzHvyT6MCttDJdK1Eh2-Zr814KL3T_Bg26sC00oIedFco7VOjnXgvfmu4UPZi1sI1D85Xzou1ErQHN-84_gWsdMgoVNrD6eXBAypoXdGY6Y782H4WUsPTGorKX2iytWQYG3YI3AT2M9pTQDsY_fRQ9Xpw_lFfx3ezyuizuYkkZncYpxzWXWZNklPBpDpnMc8xTmTKCiQRV4xp4yijUjUqo4pA00KjwPE9VLZlKRtHx9m7wf12B89XCrGwXLKsEc5yylPE8UJMtJa1xzoKqlrZ9EbavCK6G9Ksh_eo3_SDIt4J1q6H_h66Km1n5p_0Gt4mPPA</recordid><startdate>202407</startdate><enddate>202407</enddate><creator>Goswami, Lakshmi</creator><creator>Paul, Sayantan</creator><creator>Mamale, Ajay G.</creator><creator>Gonnade, Rajesh G.</creator><creator>Bhattacharya, Asish K.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0009-0009-1717-2179</orcidid><orcidid>https://orcid.org/0000-0003-4331-394X</orcidid><orcidid>https://orcid.org/0000-0001-7731-9237</orcidid><orcidid>https://orcid.org/0000-0002-2841-0197</orcidid><orcidid>https://orcid.org/0000-0002-9162-522X</orcidid></search><sort><creationdate>202407</creationdate><title>Methanesulfonic Acid‐Catalyzed Friedel‐Crafts Alkylation: Towards Sustainable Synthesis of Arylalkanes from Donor–Acceptor Cyclopropane Ketones</title><author>Goswami, Lakshmi ; Paul, Sayantan ; Mamale, Ajay G. ; Gonnade, Rajesh G. ; Bhattacharya, Asish K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2726-480b8c5d3521869e5c99084c47101cefb0be8472ebdf32f8e3dedf00784fbc7f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkylation</topic><topic>Chemical synthesis</topic><topic>Cyclopropane</topic><topic>donor–acceptor cyclopropane</topic><topic>Friedel-Crafts alkylation</topic><topic>Ketones</topic><topic>Methanesulfonic acid</topic><topic>Phenols</topic><topic>thiophenol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goswami, Lakshmi</creatorcontrib><creatorcontrib>Paul, Sayantan</creatorcontrib><creatorcontrib>Mamale, Ajay G.</creatorcontrib><creatorcontrib>Gonnade, Rajesh G.</creatorcontrib><creatorcontrib>Bhattacharya, Asish K.</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goswami, Lakshmi</au><au>Paul, Sayantan</au><au>Mamale, Ajay G.</au><au>Gonnade, Rajesh G.</au><au>Bhattacharya, Asish K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Methanesulfonic Acid‐Catalyzed Friedel‐Crafts Alkylation: Towards Sustainable Synthesis of Arylalkanes from Donor–Acceptor Cyclopropane Ketones</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2024-07</date><risdate>2024</risdate><volume>13</volume><issue>7</issue><epage>n/a</epage><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>We present herein Brønsted 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 Brønsted acid‐catalyzed Friedel‐Crafts alkylation of phenols with Donor–Acceptor cyclopropane.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202400116</doi><tpages>7</tpages><orcidid>https://orcid.org/0009-0009-1717-2179</orcidid><orcidid>https://orcid.org/0000-0003-4331-394X</orcidid><orcidid>https://orcid.org/0000-0001-7731-9237</orcidid><orcidid>https://orcid.org/0000-0002-2841-0197</orcidid><orcidid>https://orcid.org/0000-0002-9162-522X</orcidid></addata></record> |
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subjects | Alkylation Chemical synthesis Cyclopropane donor–acceptor cyclopropane Friedel-Crafts alkylation Ketones Methanesulfonic acid Phenols thiophenol |
title | Methanesulfonic Acid‐Catalyzed Friedel‐Crafts Alkylation: Towards Sustainable Synthesis of Arylalkanes from Donor–Acceptor Cyclopropane Ketones |
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