Asymmetric Construction of an Aryl‐Alkene Axis by Palladium‐Catalyzed Suzuki–Miyaura Coupling Reaction
The application of Suzuki–Miyaura coupling reaction to forge the atropisomeric biaryls has seen remarkable progress but exploration of this chemistry to directly forge chiral C(aryl)‐C(alkene) axis is underdeveloped. The replacement of arene substrates by alkenes intensifies the challenges in terms...
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| Veröffentlicht in: | Angewandte Chemie 2022-11, Vol.134 (45), p.n/a |
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| creator | Qiu, Sheng‐Qi Chen, Yu Peng, Xiang‐Jun He, Shi‐Jiang Cheng, Jun Kee Wang, Yong‐Bin Xiang, Shao‐Hua Song, Jun Yu, Peiyuan Zhang, Junmin Tan, Bin |
| description | The application of Suzuki–Miyaura coupling reaction to forge the atropisomeric biaryls has seen remarkable progress but exploration of this chemistry to directly forge chiral C(aryl)‐C(alkene) axis is underdeveloped. The replacement of arene substrates by alkenes intensifies the challenges in terms of reactivity, configurational atropostability of product and selectivity control. By meticulous ligand design and fine‐tuning of reaction parameters, we identified a highly active 3,3′‐triphenylsilyl‐substituted phosphite ligand to realize arene‐alkene Suzuki–Miyaura coupling of hindered aryl halides and vinyl boronates under very mild conditions. The axially chiral acyclic aryl‐alkenes were generated in commendable efficiency, enantioselectivity and E/Z selectivity.
The construction of axially chiral acyclic aryl‐alkene skeletons via classic Suzuki–Miyaura reaction has been challenging compared to the biaryls. Rational optimization established an enabling 3,3′‐triphenylsilyl‐substituted phosphite ligand for asymmetric coupling of hindered aryl halides and vinyl boronates under mild conditions, affording the acyclic aryl‐alkenes in good yield, atroposelectivity and E/Z selectivity. |
| doi_str_mv | 10.1002/ange.202211211 |
| format | Article |
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The construction of axially chiral acyclic aryl‐alkene skeletons via classic Suzuki–Miyaura reaction has been challenging compared to the biaryls. Rational optimization established an enabling 3,3′‐triphenylsilyl‐substituted phosphite ligand for asymmetric coupling of hindered aryl halides and vinyl boronates under mild conditions, affording the acyclic aryl‐alkenes in good yield, atroposelectivity and E/Z selectivity.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202211211</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkenes ; Aromatic compounds ; Atroposelective ; Chemical reactions ; Chemistry ; Chirality ; Coupling ; Enantiomers ; Halides ; Ligands ; Palladium ; Palladium Catalysis ; Parameter identification ; Phosphite ; Selectivity ; Substrates ; Suzuki–Miyaura Coupling</subject><ispartof>Angewandte Chemie, 2022-11, Vol.134 (45), p.n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1621-a286f99f7e0a8e7377a5f180c0d11ffcc7f257a27b2c8353fe258a01a030b5433</citedby><cites>FETCH-LOGICAL-c1621-a286f99f7e0a8e7377a5f180c0d11ffcc7f257a27b2c8353fe258a01a030b5433</cites><orcidid>0000-0001-8219-9970</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%2Fange.202211211$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.202211211$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Qiu, Sheng‐Qi</creatorcontrib><creatorcontrib>Chen, Yu</creatorcontrib><creatorcontrib>Peng, Xiang‐Jun</creatorcontrib><creatorcontrib>He, Shi‐Jiang</creatorcontrib><creatorcontrib>Cheng, Jun Kee</creatorcontrib><creatorcontrib>Wang, Yong‐Bin</creatorcontrib><creatorcontrib>Xiang, Shao‐Hua</creatorcontrib><creatorcontrib>Song, Jun</creatorcontrib><creatorcontrib>Yu, Peiyuan</creatorcontrib><creatorcontrib>Zhang, Junmin</creatorcontrib><creatorcontrib>Tan, Bin</creatorcontrib><title>Asymmetric Construction of an Aryl‐Alkene Axis by Palladium‐Catalyzed Suzuki–Miyaura Coupling Reaction</title><title>Angewandte Chemie</title><description>The application of Suzuki–Miyaura coupling reaction to forge the atropisomeric biaryls has seen remarkable progress but exploration of this chemistry to directly forge chiral C(aryl)‐C(alkene) axis is underdeveloped. The replacement of arene substrates by alkenes intensifies the challenges in terms of reactivity, configurational atropostability of product and selectivity control. By meticulous ligand design and fine‐tuning of reaction parameters, we identified a highly active 3,3′‐triphenylsilyl‐substituted phosphite ligand to realize arene‐alkene Suzuki–Miyaura coupling of hindered aryl halides and vinyl boronates under very mild conditions. The axially chiral acyclic aryl‐alkenes were generated in commendable efficiency, enantioselectivity and E/Z selectivity.
The construction of axially chiral acyclic aryl‐alkene skeletons via classic Suzuki–Miyaura reaction has been challenging compared to the biaryls. Rational optimization established an enabling 3,3′‐triphenylsilyl‐substituted phosphite ligand for asymmetric coupling of hindered aryl halides and vinyl boronates under mild conditions, affording the acyclic aryl‐alkenes in good yield, atroposelectivity and E/Z selectivity.</description><subject>Alkenes</subject><subject>Aromatic compounds</subject><subject>Atroposelective</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Chirality</subject><subject>Coupling</subject><subject>Enantiomers</subject><subject>Halides</subject><subject>Ligands</subject><subject>Palladium</subject><subject>Palladium Catalysis</subject><subject>Parameter identification</subject><subject>Phosphite</subject><subject>Selectivity</subject><subject>Substrates</subject><subject>Suzuki–Miyaura Coupling</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Kw0AUhQdRsFa3rgdcp96ZJJ1kGUKtQv3Bn3W4TWfKtJOkziRouuojCL5hn8TUii6FC3dxv3Pu4RByzmDAAPgllnM54MA5Y90ckB4LOfN8EYpD0gMIAi_iQXxMTpxbAMCQi7hHTOLaopC11TlNq9LVtslrXZW0UhRLmtjWbDcfiVnKUtLkXTs6bekDGoMz3RTdKcUaTbuWM_rUrJul3m4-b3WLjcXOr1kZXc7po8Rv01NypNA4efaz--TlavScXnuT-_FNmky8nA27yMijoYpjJSRgJIUvBIaKRZDDjDGl8lwoHgrkYsrzyA99JXkYITAEH6Zh4Pt9crH3XdnqtZGuzhZVY8vuZcaFDwGHWEQdNdhTua2cs1JlK6sLtG3GINs1mu0azX4b7QTxXvCmjWz_obPkbjz6034BKfB9zQ</recordid><startdate>20221107</startdate><enddate>20221107</enddate><creator>Qiu, Sheng‐Qi</creator><creator>Chen, Yu</creator><creator>Peng, Xiang‐Jun</creator><creator>He, Shi‐Jiang</creator><creator>Cheng, Jun Kee</creator><creator>Wang, Yong‐Bin</creator><creator>Xiang, Shao‐Hua</creator><creator>Song, Jun</creator><creator>Yu, Peiyuan</creator><creator>Zhang, Junmin</creator><creator>Tan, Bin</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-8219-9970</orcidid></search><sort><creationdate>20221107</creationdate><title>Asymmetric Construction of an Aryl‐Alkene Axis by Palladium‐Catalyzed Suzuki–Miyaura Coupling Reaction</title><author>Qiu, Sheng‐Qi ; Chen, Yu ; Peng, Xiang‐Jun ; He, Shi‐Jiang ; Cheng, Jun Kee ; Wang, Yong‐Bin ; Xiang, Shao‐Hua ; Song, Jun ; Yu, Peiyuan ; Zhang, Junmin ; Tan, Bin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1621-a286f99f7e0a8e7377a5f180c0d11ffcc7f257a27b2c8353fe258a01a030b5433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkenes</topic><topic>Aromatic compounds</topic><topic>Atroposelective</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Chirality</topic><topic>Coupling</topic><topic>Enantiomers</topic><topic>Halides</topic><topic>Ligands</topic><topic>Palladium</topic><topic>Palladium Catalysis</topic><topic>Parameter identification</topic><topic>Phosphite</topic><topic>Selectivity</topic><topic>Substrates</topic><topic>Suzuki–Miyaura Coupling</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qiu, Sheng‐Qi</creatorcontrib><creatorcontrib>Chen, Yu</creatorcontrib><creatorcontrib>Peng, Xiang‐Jun</creatorcontrib><creatorcontrib>He, Shi‐Jiang</creatorcontrib><creatorcontrib>Cheng, Jun Kee</creatorcontrib><creatorcontrib>Wang, Yong‐Bin</creatorcontrib><creatorcontrib>Xiang, Shao‐Hua</creatorcontrib><creatorcontrib>Song, Jun</creatorcontrib><creatorcontrib>Yu, Peiyuan</creatorcontrib><creatorcontrib>Zhang, Junmin</creatorcontrib><creatorcontrib>Tan, Bin</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qiu, Sheng‐Qi</au><au>Chen, Yu</au><au>Peng, Xiang‐Jun</au><au>He, Shi‐Jiang</au><au>Cheng, Jun Kee</au><au>Wang, Yong‐Bin</au><au>Xiang, Shao‐Hua</au><au>Song, Jun</au><au>Yu, Peiyuan</au><au>Zhang, Junmin</au><au>Tan, Bin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Construction of an Aryl‐Alkene Axis by Palladium‐Catalyzed Suzuki–Miyaura Coupling Reaction</atitle><jtitle>Angewandte Chemie</jtitle><date>2022-11-07</date><risdate>2022</risdate><volume>134</volume><issue>45</issue><epage>n/a</epage><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>The application of Suzuki–Miyaura coupling reaction to forge the atropisomeric biaryls has seen remarkable progress but exploration of this chemistry to directly forge chiral C(aryl)‐C(alkene) axis is underdeveloped. The replacement of arene substrates by alkenes intensifies the challenges in terms of reactivity, configurational atropostability of product and selectivity control. By meticulous ligand design and fine‐tuning of reaction parameters, we identified a highly active 3,3′‐triphenylsilyl‐substituted phosphite ligand to realize arene‐alkene Suzuki–Miyaura coupling of hindered aryl halides and vinyl boronates under very mild conditions. The axially chiral acyclic aryl‐alkenes were generated in commendable efficiency, enantioselectivity and E/Z selectivity.
The construction of axially chiral acyclic aryl‐alkene skeletons via classic Suzuki–Miyaura reaction has been challenging compared to the biaryls. Rational optimization established an enabling 3,3′‐triphenylsilyl‐substituted phosphite ligand for asymmetric coupling of hindered aryl halides and vinyl boronates under mild conditions, affording the acyclic aryl‐alkenes in good yield, atroposelectivity and E/Z selectivity.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.202211211</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-8219-9970</orcidid></addata></record> |
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| subjects | Alkenes Aromatic compounds Atroposelective Chemical reactions Chemistry Chirality Coupling Enantiomers Halides Ligands Palladium Palladium Catalysis Parameter identification Phosphite Selectivity Substrates Suzuki–Miyaura Coupling |
| title | Asymmetric Construction of an Aryl‐Alkene Axis by Palladium‐Catalyzed Suzuki–Miyaura Coupling Reaction |
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