Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation
Maleimides and succinimides are all vital scaffolds in biological fields and various natural products. Maleimide derivatives have been extensively used as coupling partners for various organic transformations, affording a broad array of important molecular architectures including succinimides. In th...
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Veröffentlicht in: | European journal of organic chemistry 2021-11, Vol.2021 (43), p.5862-5879 |
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creator | Liu, Shuang‐Liang Shi, Yajun Xue, Cong Zhang, Liming Zhou, Liming Song, Mao‐Ping |
description | Maleimides and succinimides are all vital scaffolds in biological fields and various natural products. Maleimide derivatives have been extensively used as coupling partners for various organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, a variety of efficient chelation‐assisted strategies have been employed for the selective addition of C−H bonds to maleimides giving succinimides, which are also highly important building blocks in organic synthesis. This Review provides an overview of research progress relating to maleimides participated transition‐metal‐catalyzed group‐directed C−H alkylation from 2012 to 2021. Significant advances in this field were highlighted, diverse transition metal catalysts, organic substrates contained different directing groups, reaction mechanisms as well as synthetic applications are systematically discussed. In addition, the limitations and intractable issues need to be solved in the future are also pointed out.
This Review summarizes significant advances in directing‐group‐controlled transition‐metal‐catalyzed selective C(sp2)−H/C(sp3)−H alkylation with maleimides. Catalysts, substrates, directing groups, reaction mechanisms, synthetic applications as well as limitations and intractable issues of this field were systematically discussed. |
doi_str_mv | 10.1002/ejoc.202101262 |
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This Review summarizes significant advances in directing‐group‐controlled transition‐metal‐catalyzed selective C(sp2)−H/C(sp3)−H alkylation with maleimides. Catalysts, substrates, directing groups, reaction mechanisms, synthetic applications as well as limitations and intractable issues of this field were systematically discussed.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202101262</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkylation ; Chelation ; Coupling (molecular) ; C−H Alkylation ; Directing Group ; Maleimides ; Molecular structure ; Natural products ; Reaction mechanisms ; Substrates ; Succinimides ; Transition metals ; Transition-Metal-Catalyzed</subject><ispartof>European journal of organic chemistry, 2021-11, Vol.2021 (43), p.5862-5879</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3132-24883d10805e020230a9dfc81279638512b690b0405cce7eb2033cc0055ca4833</citedby><cites>FETCH-LOGICAL-c3132-24883d10805e020230a9dfc81279638512b690b0405cce7eb2033cc0055ca4833</cites><orcidid>0000-0001-8596-3989</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%2Fejoc.202101262$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202101262$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Liu, Shuang‐Liang</creatorcontrib><creatorcontrib>Shi, Yajun</creatorcontrib><creatorcontrib>Xue, Cong</creatorcontrib><creatorcontrib>Zhang, Liming</creatorcontrib><creatorcontrib>Zhou, Liming</creatorcontrib><creatorcontrib>Song, Mao‐Ping</creatorcontrib><title>Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation</title><title>European journal of organic chemistry</title><description>Maleimides and succinimides are all vital scaffolds in biological fields and various natural products. Maleimide derivatives have been extensively used as coupling partners for various organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, a variety of efficient chelation‐assisted strategies have been employed for the selective addition of C−H bonds to maleimides giving succinimides, which are also highly important building blocks in organic synthesis. This Review provides an overview of research progress relating to maleimides participated transition‐metal‐catalyzed group‐directed C−H alkylation from 2012 to 2021. Significant advances in this field were highlighted, diverse transition metal catalysts, organic substrates contained different directing groups, reaction mechanisms as well as synthetic applications are systematically discussed. In addition, the limitations and intractable issues need to be solved in the future are also pointed out.
This Review summarizes significant advances in directing‐group‐controlled transition‐metal‐catalyzed selective C(sp2)−H/C(sp3)−H alkylation with maleimides. Catalysts, substrates, directing groups, reaction mechanisms, synthetic applications as well as limitations and intractable issues of this field were systematically discussed.</description><subject>Alkylation</subject><subject>Chelation</subject><subject>Coupling (molecular)</subject><subject>C−H Alkylation</subject><subject>Directing Group</subject><subject>Maleimides</subject><subject>Molecular structure</subject><subject>Natural products</subject><subject>Reaction mechanisms</subject><subject>Substrates</subject><subject>Succinimides</subject><subject>Transition metals</subject><subject>Transition-Metal-Catalyzed</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFULFOwzAUtBBIlMLKHIk55dlO0nisQmlBrTpQJDbLdVzk4sbFTkFhYmREfGK_BEdFMDLd07u793SH0DmGHgYgl2plZY8AwYBJRg5QBwNjMWQMDsOc0CTGjD4coxPvVwDAsgx30HIqjNJrXSof6Sq60k7JWlePu_fPkbPbTcDCVrWzxqgymjtReV1rW4X9VNXCtLwI2LwF-k6Z1v2iomL38TWOBuapMaKVn6KjpTBenf1gF91fD-fFOJ7MRjfFYBJLiimJSZLntMSQQ6ogRKEgWLmUOSZ9ltE8xWQR4iwggVRK1VcLApRKCZCmUiQ5pV10sb-7cfZ5q3zNV3brqvCSkyyUBJSl_aDq7VXSWe-dWvKN02vhGo6Bt13ytkv-22UwsL3hVRvV_KPmw9tZ8ef9Bm3mfJM</recordid><startdate>20211122</startdate><enddate>20211122</enddate><creator>Liu, Shuang‐Liang</creator><creator>Shi, Yajun</creator><creator>Xue, Cong</creator><creator>Zhang, Liming</creator><creator>Zhou, Liming</creator><creator>Song, Mao‐Ping</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8596-3989</orcidid></search><sort><creationdate>20211122</creationdate><title>Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation</title><author>Liu, Shuang‐Liang ; Shi, Yajun ; Xue, Cong ; Zhang, Liming ; Zhou, Liming ; Song, Mao‐Ping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3132-24883d10805e020230a9dfc81279638512b690b0405cce7eb2033cc0055ca4833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkylation</topic><topic>Chelation</topic><topic>Coupling (molecular)</topic><topic>C−H Alkylation</topic><topic>Directing Group</topic><topic>Maleimides</topic><topic>Molecular structure</topic><topic>Natural products</topic><topic>Reaction mechanisms</topic><topic>Substrates</topic><topic>Succinimides</topic><topic>Transition metals</topic><topic>Transition-Metal-Catalyzed</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Shuang‐Liang</creatorcontrib><creatorcontrib>Shi, Yajun</creatorcontrib><creatorcontrib>Xue, Cong</creatorcontrib><creatorcontrib>Zhang, Liming</creatorcontrib><creatorcontrib>Zhou, Liming</creatorcontrib><creatorcontrib>Song, Mao‐Ping</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Shuang‐Liang</au><au>Shi, Yajun</au><au>Xue, Cong</au><au>Zhang, Liming</au><au>Zhou, Liming</au><au>Song, Mao‐Ping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-11-22</date><risdate>2021</risdate><volume>2021</volume><issue>43</issue><spage>5862</spage><epage>5879</epage><pages>5862-5879</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Maleimides and succinimides are all vital scaffolds in biological fields and various natural products. Maleimide derivatives have been extensively used as coupling partners for various organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, a variety of efficient chelation‐assisted strategies have been employed for the selective addition of C−H bonds to maleimides giving succinimides, which are also highly important building blocks in organic synthesis. This Review provides an overview of research progress relating to maleimides participated transition‐metal‐catalyzed group‐directed C−H alkylation from 2012 to 2021. Significant advances in this field were highlighted, diverse transition metal catalysts, organic substrates contained different directing groups, reaction mechanisms as well as synthetic applications are systematically discussed. In addition, the limitations and intractable issues need to be solved in the future are also pointed out.
This Review summarizes significant advances in directing‐group‐controlled transition‐metal‐catalyzed selective C(sp2)−H/C(sp3)−H alkylation with maleimides. Catalysts, substrates, directing groups, reaction mechanisms, synthetic applications as well as limitations and intractable issues of this field were systematically discussed.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202101262</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0001-8596-3989</orcidid></addata></record> |
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subjects | Alkylation Chelation Coupling (molecular) C−H Alkylation Directing Group Maleimides Molecular structure Natural products Reaction mechanisms Substrates Succinimides Transition metals Transition-Metal-Catalyzed |
title | Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation |
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