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(SCp)Rhodium‐Catalyzed Asymmetric Satoh–Miura Reaction for Building‐up Axial Chirality: Counteranion‐Directed Switching of Reaction Pathways
Satoh–Miura reaction is an important method for extending π‐systems by forging multi‐substituted benzene rings via double aryl C−H activation and annulation with alkynes. However, the development of highly enantioselective Satoh–Miura reaction remains rather challenging. Herein, we report an asymmet...
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Published in: | Angewandte Chemie International Edition 2023-01, Vol.62 (3), p.e202214460-n/a |
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description | Satoh–Miura reaction is an important method for extending π‐systems by forging multi‐substituted benzene rings via double aryl C−H activation and annulation with alkynes. However, the development of highly enantioselective Satoh–Miura reaction remains rather challenging. Herein, we report an asymmetric Satoh–Miura reaction between 1‐aryl benzo[h]isoquinolines and internal alkynes enabled by a SCpRh‐catalyst. Judiciously choosing the counteranion of the Rh‐catalyst is crucial for the desired reactivity over the competitive formation of azoniahelicenes. Detailed mechanistic studies support the proposal of counteranion‐directed switching of reaction pathways in Rh‐catalyzed asymmetric C−H activation.
A highly enantioselective Satoh–Miura reaction enabled by a chiral tri‐substituted SCpRh(III)‐catalyst is described. The desired axially chiral products can be afforded in moderate to excellent yields (up to 85 %) and excellent enantioselectivity (up to 96 % ee). Meanwhile, DFT calculations provide rationales behind this unique phenomenon of counteranion‐directed switching of the pathways in C−H activation reactions. |
doi_str_mv | 10.1002/anie.202214460 |
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A highly enantioselective Satoh–Miura reaction enabled by a chiral tri‐substituted SCpRh(III)‐catalyst is described. The desired axially chiral products can be afforded in moderate to excellent yields (up to 85 %) and excellent enantioselectivity (up to 96 % ee). Meanwhile, DFT calculations provide rationales behind this unique phenomenon of counteranion‐directed switching of the pathways in C−H activation reactions.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202214460</identifier><identifier>PMID: 36383091</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Aromatic compounds ; Asymmetric Catalysis ; Asymmetry ; Benzene ; Catalysts ; Chemical reactions ; Chirality ; Counteranion ; C−H Activation ; Enantiomers ; Forging ; Rhodium ; Rhodium Catalysis ; Satoh–Miura Reaction ; Switching</subject><ispartof>Angewandte Chemie International Edition, 2023-01, Vol.62 (3), p.e202214460-n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><rights>2022 Wiley-VCH GmbH.</rights><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3730-d1b3ef5f658f2504cbfc60e298c76f790540a55f25daa3f5e231b79acccb387d3</citedby><cites>FETCH-LOGICAL-c3730-d1b3ef5f658f2504cbfc60e298c76f790540a55f25daa3f5e231b79acccb387d3</cites><orcidid>0000-0003-4586-8359</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36383091$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Wen‐Wen</creatorcontrib><creatorcontrib>Wang, Qiang</creatorcontrib><creatorcontrib>Zhang, Su‐Zhen</creatorcontrib><creatorcontrib>Zheng, Chao</creatorcontrib><creatorcontrib>You, Shu‐Li</creatorcontrib><title>(SCp)Rhodium‐Catalyzed Asymmetric Satoh–Miura Reaction for Building‐up Axial Chirality: Counteranion‐Directed Switching of Reaction Pathways</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Satoh–Miura reaction is an important method for extending π‐systems by forging multi‐substituted benzene rings via double aryl C−H activation and annulation with alkynes. However, the development of highly enantioselective Satoh–Miura reaction remains rather challenging. Herein, we report an asymmetric Satoh–Miura reaction between 1‐aryl benzo[h]isoquinolines and internal alkynes enabled by a SCpRh‐catalyst. Judiciously choosing the counteranion of the Rh‐catalyst is crucial for the desired reactivity over the competitive formation of azoniahelicenes. Detailed mechanistic studies support the proposal of counteranion‐directed switching of reaction pathways in Rh‐catalyzed asymmetric C−H activation.
A highly enantioselective Satoh–Miura reaction enabled by a chiral tri‐substituted SCpRh(III)‐catalyst is described. The desired axially chiral products can be afforded in moderate to excellent yields (up to 85 %) and excellent enantioselectivity (up to 96 % ee). Meanwhile, DFT calculations provide rationales behind this unique phenomenon of counteranion‐directed switching of the pathways in C−H activation reactions.</description><subject>Alkynes</subject><subject>Aromatic compounds</subject><subject>Asymmetric Catalysis</subject><subject>Asymmetry</subject><subject>Benzene</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chirality</subject><subject>Counteranion</subject><subject>C−H Activation</subject><subject>Enantiomers</subject><subject>Forging</subject><subject>Rhodium</subject><subject>Rhodium Catalysis</subject><subject>Satoh–Miura Reaction</subject><subject>Switching</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkctu1DAUhi1E1ZbSLUtkiU1ZZPAljhN2QyhQqVzUgXXkODZxlcRTXzRNV30EJHjCPkldTWklNqyOpfP9n478A_ACowVGiLwRk1ELggjBeV6gJ2AfM4Izyjl9mt45pRkvGd4Dz7w_T3xZomIX7NGClhRVeB_8OVrV69dnve1MHG-uf9UiiGG-Uh1c-nkcVXBGwpUItr-5_v3ZRCfgmRIyGDtBbR18F83QmelnisY1XF4aMcC6N04MJsxvYW3jFJRLV9opIe-NUzIk-WpjguxTDlr9KPwmQr8Rs38OdrQYvDq8nwfgx4fj7_Wn7PTrx5N6eZpJyinKOtxSpZkuWKkJQ7lstSyQIlUpeaF5hViOBGNp1wlBNVOE4pZXQkrZ0pJ39AAcbb1rZy-i8qEZjZdqGMSkbPQN4ZRjzBHPE_rqH_TcRjel6xJV4Kos0z8narGlpLPeO6WbtTOjcHODUXPXV3PXV_PQVwq8vNfGdlTdA_63oARUW2BjBjX_R9csv5wcP8pvAVuMp6g</recordid><startdate>20230116</startdate><enddate>20230116</enddate><creator>Zhang, Wen‐Wen</creator><creator>Wang, Qiang</creator><creator>Zhang, Su‐Zhen</creator><creator>Zheng, Chao</creator><creator>You, Shu‐Li</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4586-8359</orcidid></search><sort><creationdate>20230116</creationdate><title>(SCp)Rhodium‐Catalyzed Asymmetric Satoh–Miura Reaction for Building‐up Axial Chirality: Counteranion‐Directed Switching of Reaction Pathways</title><author>Zhang, Wen‐Wen ; Wang, Qiang ; Zhang, Su‐Zhen ; Zheng, Chao ; You, Shu‐Li</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3730-d1b3ef5f658f2504cbfc60e298c76f790540a55f25daa3f5e231b79acccb387d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkynes</topic><topic>Aromatic compounds</topic><topic>Asymmetric Catalysis</topic><topic>Asymmetry</topic><topic>Benzene</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Chirality</topic><topic>Counteranion</topic><topic>C−H Activation</topic><topic>Enantiomers</topic><topic>Forging</topic><topic>Rhodium</topic><topic>Rhodium Catalysis</topic><topic>Satoh–Miura Reaction</topic><topic>Switching</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Wen‐Wen</creatorcontrib><creatorcontrib>Wang, Qiang</creatorcontrib><creatorcontrib>Zhang, Su‐Zhen</creatorcontrib><creatorcontrib>Zheng, Chao</creatorcontrib><creatorcontrib>You, Shu‐Li</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Wen‐Wen</au><au>Wang, Qiang</au><au>Zhang, Su‐Zhen</au><au>Zheng, Chao</au><au>You, Shu‐Li</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(SCp)Rhodium‐Catalyzed Asymmetric Satoh–Miura Reaction for Building‐up Axial Chirality: Counteranion‐Directed Switching of Reaction Pathways</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2023-01-16</date><risdate>2023</risdate><volume>62</volume><issue>3</issue><spage>e202214460</spage><epage>n/a</epage><pages>e202214460-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Satoh–Miura reaction is an important method for extending π‐systems by forging multi‐substituted benzene rings via double aryl C−H activation and annulation with alkynes. However, the development of highly enantioselective Satoh–Miura reaction remains rather challenging. Herein, we report an asymmetric Satoh–Miura reaction between 1‐aryl benzo[h]isoquinolines and internal alkynes enabled by a SCpRh‐catalyst. Judiciously choosing the counteranion of the Rh‐catalyst is crucial for the desired reactivity over the competitive formation of azoniahelicenes. Detailed mechanistic studies support the proposal of counteranion‐directed switching of reaction pathways in Rh‐catalyzed asymmetric C−H activation.
A highly enantioselective Satoh–Miura reaction enabled by a chiral tri‐substituted SCpRh(III)‐catalyst is described. The desired axially chiral products can be afforded in moderate to excellent yields (up to 85 %) and excellent enantioselectivity (up to 96 % ee). Meanwhile, DFT calculations provide rationales behind this unique phenomenon of counteranion‐directed switching of the pathways in C−H activation reactions.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36383091</pmid><doi>10.1002/anie.202214460</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0003-4586-8359</orcidid></addata></record> |
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subjects | Alkynes Aromatic compounds Asymmetric Catalysis Asymmetry Benzene Catalysts Chemical reactions Chirality Counteranion C−H Activation Enantiomers Forging Rhodium Rhodium Catalysis Satoh–Miura Reaction Switching |
title | (SCp)Rhodium‐Catalyzed Asymmetric Satoh–Miura Reaction for Building‐up Axial Chirality: Counteranion‐Directed Switching of Reaction Pathways |
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