Gold‐Catalyzed Arylative Cope Rearrangement
Cope rearrangements have garnered significant attention owing to their ability to undergo structural reorganization in stereoselective manner. While substantial advances have been achieved over decades, these rearrangements remained applicable exclusively to parent 1,5‐hexadienes. Herein, we disclos...
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| Veröffentlicht in: | Angewandte Chemie 2024-08, Vol.136 (33), p.n/a |
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| creator | Paroi, Bidisha Pegu, Chayanika Mane, Manoj V. Patil, Nitin T. |
| description | Cope rearrangements have garnered significant attention owing to their ability to undergo structural reorganization in stereoselective manner. While substantial advances have been achieved over decades, these rearrangements remained applicable exclusively to parent 1,5‐hexadienes. Herein, we disclose the gold‐catalyzed arylative Cope rearrangement of 1,6‐heptadienes via a cyclization‐induced [3,3]‐rearrangement employing ligand‐enabled gold redox catalysis. Detailed mechanistic investigations including several control experiments, cross‐over experiment, HRMS analysis, 31P NMR and DFT studies have been performed to underpin the mechanism.
Reported herein is the arylative Cope rearrangement of 1,6‐heptadienes facilitated by ligand‐enabled redox gold catalysis. Unlike the classical Cope rearrangement involving 1,5‐hexadienes, a cyclization‐induced [3,3]‐rearrangement of 1,6‐heptadienes using the merger of π‐activation and cross‐coupling reactivity, has been achieved. |
| doi_str_mv | 10.1002/ange.202406936 |
| format | Article |
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Reported herein is the arylative Cope rearrangement of 1,6‐heptadienes facilitated by ligand‐enabled redox gold catalysis. Unlike the classical Cope rearrangement involving 1,5‐hexadienes, a cyclization‐induced [3,3]‐rearrangement of 1,6‐heptadienes using the merger of π‐activation and cross‐coupling reactivity, has been achieved.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202406936</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Catalysis ; Cope rearrangement ; cross-coupling ; Gold ; gold catalysis ; NMR ; Nuclear magnetic resonance ; redox catalysis ; Stereoselectivity ; π-activation</subject><ispartof>Angewandte Chemie, 2024-08, Vol.136 (33), p.n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1176-1fd570771ad98a74d9757b51ec09036c505e4cd9545f1fd18901b1455bd2a77c3</cites><orcidid>0000-0002-8372-2759 ; 0009-0004-5431-132X ; 0000-0001-8236-3638 ; 0009-0009-2479-120X</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.202406936$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.202406936$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27907,27908,45557,45558</link.rule.ids></links><search><creatorcontrib>Paroi, Bidisha</creatorcontrib><creatorcontrib>Pegu, Chayanika</creatorcontrib><creatorcontrib>Mane, Manoj V.</creatorcontrib><creatorcontrib>Patil, Nitin T.</creatorcontrib><title>Gold‐Catalyzed Arylative Cope Rearrangement</title><title>Angewandte Chemie</title><description>Cope rearrangements have garnered significant attention owing to their ability to undergo structural reorganization in stereoselective manner. While substantial advances have been achieved over decades, these rearrangements remained applicable exclusively to parent 1,5‐hexadienes. Herein, we disclose the gold‐catalyzed arylative Cope rearrangement of 1,6‐heptadienes via a cyclization‐induced [3,3]‐rearrangement employing ligand‐enabled gold redox catalysis. Detailed mechanistic investigations including several control experiments, cross‐over experiment, HRMS analysis, 31P NMR and DFT studies have been performed to underpin the mechanism.
Reported herein is the arylative Cope rearrangement of 1,6‐heptadienes facilitated by ligand‐enabled redox gold catalysis. Unlike the classical Cope rearrangement involving 1,5‐hexadienes, a cyclization‐induced [3,3]‐rearrangement of 1,6‐heptadienes using the merger of π‐activation and cross‐coupling reactivity, has been achieved.</description><subject>Catalysis</subject><subject>Cope rearrangement</subject><subject>cross-coupling</subject><subject>Gold</subject><subject>gold catalysis</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>redox catalysis</subject><subject>Stereoselectivity</subject><subject>π-activation</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Kw0AUhQdRMFa3rguuE--dzE9mGUJNhaIguh6mMxNpSZs6SZW48hF8Rp_ElIguXd3N9517OIRcIiQIQK_N9tknFCgDoVJxRCLkFONUcnlMIgDG4owydUrO2nYNAIJKFZG4bGr39fFZmM7U_bt30zz0telWr35aNDs_ffAmhEP0xm-7c3JSmbr1Fz93Qp5uZo_FPF7cl7dFvogtohQxVo5LkBKNU5mRzKmhxJKjt6AgFZYD98w6xRmvBhYzBbhExvnSUSOlTSfkaszdheZl79tOr5t92A4vdQqZVJRlUgxUMlI2NG0bfKV3YbUxodcI-jCJPvTWv5MMghqFt1Xt-39ond-Vsz_3G3hYZEk</recordid><startdate>20240812</startdate><enddate>20240812</enddate><creator>Paroi, Bidisha</creator><creator>Pegu, Chayanika</creator><creator>Mane, Manoj V.</creator><creator>Patil, Nitin T.</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/0000-0002-8372-2759</orcidid><orcidid>https://orcid.org/0009-0004-5431-132X</orcidid><orcidid>https://orcid.org/0000-0001-8236-3638</orcidid><orcidid>https://orcid.org/0009-0009-2479-120X</orcidid></search><sort><creationdate>20240812</creationdate><title>Gold‐Catalyzed Arylative Cope Rearrangement</title><author>Paroi, Bidisha ; Pegu, Chayanika ; Mane, Manoj V. ; Patil, Nitin T.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1176-1fd570771ad98a74d9757b51ec09036c505e4cd9545f1fd18901b1455bd2a77c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Catalysis</topic><topic>Cope rearrangement</topic><topic>cross-coupling</topic><topic>Gold</topic><topic>gold catalysis</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>redox catalysis</topic><topic>Stereoselectivity</topic><topic>π-activation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Paroi, Bidisha</creatorcontrib><creatorcontrib>Pegu, Chayanika</creatorcontrib><creatorcontrib>Mane, Manoj V.</creatorcontrib><creatorcontrib>Patil, Nitin T.</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>Paroi, Bidisha</au><au>Pegu, Chayanika</au><au>Mane, Manoj V.</au><au>Patil, Nitin T.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Gold‐Catalyzed Arylative Cope Rearrangement</atitle><jtitle>Angewandte Chemie</jtitle><date>2024-08-12</date><risdate>2024</risdate><volume>136</volume><issue>33</issue><epage>n/a</epage><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Cope rearrangements have garnered significant attention owing to their ability to undergo structural reorganization in stereoselective manner. While substantial advances have been achieved over decades, these rearrangements remained applicable exclusively to parent 1,5‐hexadienes. Herein, we disclose the gold‐catalyzed arylative Cope rearrangement of 1,6‐heptadienes via a cyclization‐induced [3,3]‐rearrangement employing ligand‐enabled gold redox catalysis. Detailed mechanistic investigations including several control experiments, cross‐over experiment, HRMS analysis, 31P NMR and DFT studies have been performed to underpin the mechanism.
Reported herein is the arylative Cope rearrangement of 1,6‐heptadienes facilitated by ligand‐enabled redox gold catalysis. Unlike the classical Cope rearrangement involving 1,5‐hexadienes, a cyclization‐induced [3,3]‐rearrangement of 1,6‐heptadienes using the merger of π‐activation and cross‐coupling reactivity, has been achieved.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.202406936</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-8372-2759</orcidid><orcidid>https://orcid.org/0009-0004-5431-132X</orcidid><orcidid>https://orcid.org/0000-0001-8236-3638</orcidid><orcidid>https://orcid.org/0009-0009-2479-120X</orcidid></addata></record> |
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| subjects | Catalysis Cope rearrangement cross-coupling Gold gold catalysis NMR Nuclear magnetic resonance redox catalysis Stereoselectivity π-activation |
| title | Gold‐Catalyzed Arylative Cope Rearrangement |
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