TfOH-catalyzed direct Michael addition and cascade cyclization reactions of unactivated ketones: A divergent route to functionalized benzofurans and benzofuro[3,2-b]pyridines
TfOH-catalyzed direct Michael addition and cascade cyclization reactions of azadienes with unactivated ketones have been developed by controlling the amount of TfOH, which provide a divergent approach to 2,3-disubstituted benzofurans and benzofuro[3,2-b]pyridines. Due to their weak nucleophilicity,...
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| Veröffentlicht in: | Tetrahedron 2023-05, Vol.137, p.133394, Article 133394 |
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| creator | Sun, Manman Gui, Jing Zhong, Rong Wu, Haijian Liu, Saimei Li, Jinshan Yang, Jianguo Wang, Zhiming |
| description | TfOH-catalyzed direct Michael addition and cascade cyclization reactions of azadienes with unactivated ketones have been developed by controlling the amount of TfOH, which provide a divergent approach to 2,3-disubstituted benzofurans and benzofuro[3,2-b]pyridines. Due to their weak nucleophilicity, unactivated ketones are used for the first time to react with azadienes instead of preactivated carbonyl compounds, in which the catalyst acidity is a key parameter. This approach with commercial ketones in mild reaction conditions shows synthetic and environmentally benign advantages including metal-free catalyst, atom economy and simple operation.
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| doi_str_mv | 10.1016/j.tet.2023.133394 |
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[Display omitted]</description><subject>acidity</subject><subject>Azadiene</subject><subject>benzofurans</subject><subject>Brønsted acid</subject><subject>Cascade cyclization</subject><subject>catalysts</subject><subject>cyclization reactions</subject><subject>Ketone</subject><subject>Lewis bases</subject><subject>Michael addition</subject><subject>pyridines</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1DAUhSMEEkPLA7DzkgUZrn_G48CqqoAiteqmrCpkOfYNeEjtwXZGmnmoPiNOA1tW9rHO-a6uT9O8obCmQOX73bpgWTNgfE0555141qyokKLdCCqfNysAAa0ABi-bVznvAIBSxlfN491we9VaU8x4PKEjzie0hdx4-9PgSIxzvvgYiAmOWJOtcUjs0Y7-ZJ7eExo7XzKJA5nCLA6mVNAvLDFg_kAuKvOA6QeGQlKcCpISyTCFp5ipoGruMZziMCVTOfOkfzre83es7b_vj8k7X3HnzYvBjBlf_z3Pmm-fP91dXrXXt1--Xl5ct5YpVlolEMTAqNpaYbncOtNL4JvOOGZg08vOMeZ6AGkVU12PalDdFhi1UkgpheJnzduFu0_x94S56AefLY6jCRinrJniggHdbmi10sVqU8w54aD3yT-YdNQU9NyN3unajZ670Us3NfNxyWDd4eAx6Ww9BovL92sX_X_SfwDW6JqK</recordid><startdate>20230512</startdate><enddate>20230512</enddate><creator>Sun, Manman</creator><creator>Gui, Jing</creator><creator>Zhong, Rong</creator><creator>Wu, Haijian</creator><creator>Liu, Saimei</creator><creator>Li, Jinshan</creator><creator>Yang, Jianguo</creator><creator>Wang, Zhiming</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20230512</creationdate><title>TfOH-catalyzed direct Michael addition and cascade cyclization reactions of unactivated ketones: A divergent route to functionalized benzofurans and benzofuro[3,2-b]pyridines</title><author>Sun, Manman ; Gui, Jing ; Zhong, Rong ; Wu, Haijian ; Liu, Saimei ; Li, Jinshan ; Yang, Jianguo ; Wang, Zhiming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c282t-84e04f2187c4c367dab60359ad2a05b69d22db006c8289be8f897021c64666483</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>acidity</topic><topic>Azadiene</topic><topic>benzofurans</topic><topic>Brønsted acid</topic><topic>Cascade cyclization</topic><topic>catalysts</topic><topic>cyclization reactions</topic><topic>Ketone</topic><topic>Lewis bases</topic><topic>Michael addition</topic><topic>pyridines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Manman</creatorcontrib><creatorcontrib>Gui, Jing</creatorcontrib><creatorcontrib>Zhong, Rong</creatorcontrib><creatorcontrib>Wu, Haijian</creatorcontrib><creatorcontrib>Liu, Saimei</creatorcontrib><creatorcontrib>Li, Jinshan</creatorcontrib><creatorcontrib>Yang, Jianguo</creatorcontrib><creatorcontrib>Wang, Zhiming</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Manman</au><au>Gui, Jing</au><au>Zhong, Rong</au><au>Wu, Haijian</au><au>Liu, Saimei</au><au>Li, Jinshan</au><au>Yang, Jianguo</au><au>Wang, Zhiming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>TfOH-catalyzed direct Michael addition and cascade cyclization reactions of unactivated ketones: A divergent route to functionalized benzofurans and benzofuro[3,2-b]pyridines</atitle><jtitle>Tetrahedron</jtitle><date>2023-05-12</date><risdate>2023</risdate><volume>137</volume><spage>133394</spage><pages>133394-</pages><artnum>133394</artnum><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>TfOH-catalyzed direct Michael addition and cascade cyclization reactions of azadienes with unactivated ketones have been developed by controlling the amount of TfOH, which provide a divergent approach to 2,3-disubstituted benzofurans and benzofuro[3,2-b]pyridines. Due to their weak nucleophilicity, unactivated ketones are used for the first time to react with azadienes instead of preactivated carbonyl compounds, in which the catalyst acidity is a key parameter. This approach with commercial ketones in mild reaction conditions shows synthetic and environmentally benign advantages including metal-free catalyst, atom economy and simple operation.
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| subjects | acidity Azadiene benzofurans Brønsted acid Cascade cyclization catalysts cyclization reactions Ketone Lewis bases Michael addition pyridines |
| title | TfOH-catalyzed direct Michael addition and cascade cyclization reactions of unactivated ketones: A divergent route to functionalized benzofurans and benzofuro[3,2-b]pyridines |
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