Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides
Non‐activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper‐catalyzed cross‐coupling with aryl boron compounds and alkyl 9‐BBN reagents (see scheme; 9‐BBN=9‐borabicyclo[3.3.1]nonane). The reactions proceed with practically useful r...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2011-04, Vol.50 (17), p.3904-3907 |
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| creator | Yang, Chu-Ting Zhang, Zhen-Qi Liu, Yu-Chen Liu, Lei |
| description | Non‐activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper‐catalyzed cross‐coupling with aryl boron compounds and alkyl 9‐BBN reagents (see scheme; 9‐BBN=9‐borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium‐ and nickel‐catalyzed Suzuki–Miyaura coupling reactions of alkyl halides. |
| doi_str_mv | 10.1002/anie.201008007 |
| format | Article |
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The reactions proceed with practically useful reactivities and thus complement palladium‐ and nickel‐catalyzed Suzuki–Miyaura coupling reactions of alkyl halides.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201008007</identifier><identifier>PMID: 21455914</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>alkyl halides ; alkyl pseudohalides ; Boron Compounds - chemistry ; Catalysis ; copper ; Copper - chemistry ; cross-coupling ; Cross-Linking Reagents - chemistry ; Halides ; Hydrocarbons, Halogenated - chemistry ; Molecular Structure ; organoboron compounds</subject><ispartof>Angewandte Chemie International Edition, 2011-04, Vol.50 (17), p.3904-3907</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. 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KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4107-28ed19b826c8044ee7f6196e268eacbeb2036ae92f67ebf83040d16cdb1ac1453</citedby><cites>FETCH-LOGICAL-c4107-28ed19b826c8044ee7f6196e268eacbeb2036ae92f67ebf83040d16cdb1ac1453</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201008007$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201008007$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21455914$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Chu-Ting</creatorcontrib><creatorcontrib>Zhang, Zhen-Qi</creatorcontrib><creatorcontrib>Liu, Yu-Chen</creatorcontrib><creatorcontrib>Liu, Lei</creatorcontrib><title>Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Non‐activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper‐catalyzed cross‐coupling with aryl boron compounds and alkyl 9‐BBN reagents (see scheme; 9‐BBN=9‐borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium‐ and nickel‐catalyzed Suzuki–Miyaura coupling reactions of alkyl halides.</description><subject>alkyl halides</subject><subject>alkyl pseudohalides</subject><subject>Boron Compounds - chemistry</subject><subject>Catalysis</subject><subject>copper</subject><subject>Copper - chemistry</subject><subject>cross-coupling</subject><subject>Cross-Linking Reagents - chemistry</subject><subject>Halides</subject><subject>Hydrocarbons, Halogenated - chemistry</subject><subject>Molecular Structure</subject><subject>organoboron compounds</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1v1DAQxS0EoqVw5YgsceCUxR-J7RyXqLSVVm1BII6WE09at944tROV5a_Hq5QV4sLJ49HvPc3MQ-gtJStKCPtoBgcrRnKtCJHP0DGtGC24lPx5rkvOC6kqeoRepXSXeaWIeImOGC2rqqblMRqaMI4Qi8ZMxu9-gcVNDCkVTZhH74Yb_BVMN7kw4NDjq3hjhtCGmL9N2I5hHmzCj266xdfRbU3c4bW_33l8bryzkLAZLL5OMNtwu3Reoxe98QnePL0n6Pvn02_NebG5Orto1puiKymRBVNgad0qJjpFyhJA9oLWAphQeZwWWka4MFCzXkhoe8VJSSwVnW2p6fJu_AR9WHzHGB5mSJPeutSB92aAMCetBGNCVpJn8v0_5F2Y45CH05RKykumaJ2p1UJ1--tE6PW4LKwp0fsg9D4IfQgiC9492c7tFuwB_3P5DNQL8Og87P5jp9eXF6d_mxeL1qUJfh60Jt5rIbms9I_LMy2qavPlk2K65r8B_DekLg</recordid><startdate>20110418</startdate><enddate>20110418</enddate><creator>Yang, Chu-Ting</creator><creator>Zhang, Zhen-Qi</creator><creator>Liu, Yu-Chen</creator><creator>Liu, Lei</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20110418</creationdate><title>Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides</title><author>Yang, Chu-Ting ; Zhang, Zhen-Qi ; Liu, Yu-Chen ; Liu, Lei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4107-28ed19b826c8044ee7f6196e268eacbeb2036ae92f67ebf83040d16cdb1ac1453</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>alkyl halides</topic><topic>alkyl pseudohalides</topic><topic>Boron Compounds - chemistry</topic><topic>Catalysis</topic><topic>copper</topic><topic>Copper - chemistry</topic><topic>cross-coupling</topic><topic>Cross-Linking Reagents - chemistry</topic><topic>Halides</topic><topic>Hydrocarbons, Halogenated - chemistry</topic><topic>Molecular Structure</topic><topic>organoboron compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Chu-Ting</creatorcontrib><creatorcontrib>Zhang, Zhen-Qi</creatorcontrib><creatorcontrib>Liu, Yu-Chen</creatorcontrib><creatorcontrib>Liu, Lei</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><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>Yang, Chu-Ting</au><au>Zhang, Zhen-Qi</au><au>Liu, Yu-Chen</au><au>Liu, Lei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2011-04-18</date><risdate>2011</risdate><volume>50</volume><issue>17</issue><spage>3904</spage><epage>3907</epage><pages>3904-3907</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Non‐activated alkyl electrophiles, including alkyl iodides, bromides, tosylates, mesylates, and even chlorides, underwent copper‐catalyzed cross‐coupling with aryl boron compounds and alkyl 9‐BBN reagents (see scheme; 9‐BBN=9‐borabicyclo[3.3.1]nonane). The reactions proceed with practically useful reactivities and thus complement palladium‐ and nickel‐catalyzed Suzuki–Miyaura coupling reactions of alkyl halides.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21455914</pmid><doi>10.1002/anie.201008007</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record> |
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| language | eng |
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| source | MEDLINE; Access via Wiley Online Library |
| subjects | alkyl halides alkyl pseudohalides Boron Compounds - chemistry Catalysis copper Copper - chemistry cross-coupling Cross-Linking Reagents - chemistry Halides Hydrocarbons, Halogenated - chemistry Molecular Structure organoboron compounds |
| title | Copper-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Primary Alkyl Halides and Pseudohalides |
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