Transition-Metal-Catalyzed C–H Alkylation Using Alkenes
Alkylation reactions represent an important organic transformation to form C–C bonds. In addition to conventional approaches with alkyl halides or sulfonates as alkylating agents, the use of unactivated olefins for alkylations has become attractive from both cost and sustainability viewpoints. This...
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Veröffentlicht in: | Chemical reviews 2017-07, Vol.117 (13), p.9333-9403 |
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description | Alkylation reactions represent an important organic transformation to form C–C bonds. In addition to conventional approaches with alkyl halides or sulfonates as alkylating agents, the use of unactivated olefins for alkylations has become attractive from both cost and sustainability viewpoints. This Review summarizes transition-metal-catalyzed alkylations of various carbon–hydrogen bonds (addition of C–H bonds across olefins) using regular olefins or 1,3-dienes up to May 2016. According to the mode of activation, the Review is divided into two sections: alkylation via C–H activation and alkylation via olefin activation. |
doi_str_mv | 10.1021/acs.chemrev.6b00574 |
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In addition to conventional approaches with alkyl halides or sulfonates as alkylating agents, the use of unactivated olefins for alkylations has become attractive from both cost and sustainability viewpoints. This Review summarizes transition-metal-catalyzed alkylations of various carbon–hydrogen bonds (addition of C–H bonds across olefins) using regular olefins or 1,3-dienes up to May 2016. According to the mode of activation, the Review is divided into two sections: alkylation via C–H activation and alkylation via olefin activation.</description><identifier>ISSN: 0009-2665</identifier><identifier>EISSN: 1520-6890</identifier><identifier>DOI: 10.1021/acs.chemrev.6b00574</identifier><identifier>PMID: 28125210</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Activation ; Alkenes ; Alkylation ; Bonding ; Carbon ; Catalysis ; Chemical reactions ; Dienes ; Halides ; Hydrocarbons ; Hydrogen bonds ; Metals ; Reagents ; Sulfonates ; Sustainability</subject><ispartof>Chemical reviews, 2017-07, Vol.117 (13), p.9333-9403</ispartof><rights>Copyright © 2017 American Chemical Society</rights><rights>Copyright American Chemical Society Jul 12, 2017</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a439t-89dedd6e4845ba9c321de2e31ec0819c81dae0f5021f7d1df9441577141d19a53</citedby><cites>FETCH-LOGICAL-a439t-89dedd6e4845ba9c321de2e31ec0819c81dae0f5021f7d1df9441577141d19a53</cites><orcidid>0000-0003-1331-6015</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.chemrev.6b00574$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.chemrev.6b00574$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28125210$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dong, Zhe</creatorcontrib><creatorcontrib>Ren, Zhi</creatorcontrib><creatorcontrib>Thompson, Samuel J</creatorcontrib><creatorcontrib>Xu, Yan</creatorcontrib><creatorcontrib>Dong, Guangbin</creatorcontrib><title>Transition-Metal-Catalyzed C–H Alkylation Using Alkenes</title><title>Chemical reviews</title><addtitle>Chem. Rev</addtitle><description>Alkylation reactions represent an important organic transformation to form C–C bonds. In addition to conventional approaches with alkyl halides or sulfonates as alkylating agents, the use of unactivated olefins for alkylations has become attractive from both cost and sustainability viewpoints. This Review summarizes transition-metal-catalyzed alkylations of various carbon–hydrogen bonds (addition of C–H bonds across olefins) using regular olefins or 1,3-dienes up to May 2016. According to the mode of activation, the Review is divided into two sections: alkylation via C–H activation and alkylation via olefin activation.</description><subject>Activation</subject><subject>Alkenes</subject><subject>Alkylation</subject><subject>Bonding</subject><subject>Carbon</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Dienes</subject><subject>Halides</subject><subject>Hydrocarbons</subject><subject>Hydrogen bonds</subject><subject>Metals</subject><subject>Reagents</subject><subject>Sulfonates</subject><subject>Sustainability</subject><issn>0009-2665</issn><issn>1520-6890</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kM1KAzEURoMotlafQJCCGzfT3ptJZibLUtQKFTftOqSTOzp1fupkKtSV7-Ab-iSmtCq4cJOQcL7vJoexc4QBAsehSd0gfaKyoddBtACQsThgXZQcgihRcMi6AKACHkWyw06cW_qjlDw-Zh2eIJccocvUrDGVy9u8roJ7ak0RjI1fN29k--PP949Jf1Q8bwqzBfpzl1eP2wuqyJ2yo8wUjs72e4_Nb65n40kwfbi9G4-mgRGhaoNEWbI2IpEIuTAqDTla4hQipZCgShO0hiCT_kdZbNFmSgiUcYwCLSojwx672vWumvplTa7VZe5SKgpTUb12GpMYEgEQgkcv_6DLet1U_nUaVYTCc0J4KtxRaVM711CmV01emmajEfTWrPZm9d6s3pv1qYt993pRkv3JfKv0wHAHbNO_c_-p_AJL4YYq</recordid><startdate>20170712</startdate><enddate>20170712</enddate><creator>Dong, Zhe</creator><creator>Ren, Zhi</creator><creator>Thompson, Samuel J</creator><creator>Xu, Yan</creator><creator>Dong, Guangbin</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1331-6015</orcidid></search><sort><creationdate>20170712</creationdate><title>Transition-Metal-Catalyzed C–H Alkylation Using Alkenes</title><author>Dong, Zhe ; Ren, Zhi ; Thompson, Samuel J ; Xu, Yan ; Dong, Guangbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a439t-89dedd6e4845ba9c321de2e31ec0819c81dae0f5021f7d1df9441577141d19a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Activation</topic><topic>Alkenes</topic><topic>Alkylation</topic><topic>Bonding</topic><topic>Carbon</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Dienes</topic><topic>Halides</topic><topic>Hydrocarbons</topic><topic>Hydrogen bonds</topic><topic>Metals</topic><topic>Reagents</topic><topic>Sulfonates</topic><topic>Sustainability</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dong, Zhe</creatorcontrib><creatorcontrib>Ren, Zhi</creatorcontrib><creatorcontrib>Thompson, Samuel J</creatorcontrib><creatorcontrib>Xu, Yan</creatorcontrib><creatorcontrib>Dong, Guangbin</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical reviews</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dong, Zhe</au><au>Ren, Zhi</au><au>Thompson, Samuel J</au><au>Xu, Yan</au><au>Dong, Guangbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition-Metal-Catalyzed C–H Alkylation Using Alkenes</atitle><jtitle>Chemical reviews</jtitle><addtitle>Chem. Rev</addtitle><date>2017-07-12</date><risdate>2017</risdate><volume>117</volume><issue>13</issue><spage>9333</spage><epage>9403</epage><pages>9333-9403</pages><issn>0009-2665</issn><eissn>1520-6890</eissn><abstract>Alkylation reactions represent an important organic transformation to form C–C bonds. In addition to conventional approaches with alkyl halides or sulfonates as alkylating agents, the use of unactivated olefins for alkylations has become attractive from both cost and sustainability viewpoints. This Review summarizes transition-metal-catalyzed alkylations of various carbon–hydrogen bonds (addition of C–H bonds across olefins) using regular olefins or 1,3-dienes up to May 2016. 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subjects | Activation Alkenes Alkylation Bonding Carbon Catalysis Chemical reactions Dienes Halides Hydrocarbons Hydrogen bonds Metals Reagents Sulfonates Sustainability |
title | Transition-Metal-Catalyzed C–H Alkylation Using Alkenes |
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