Direct Oxidative Arylation of Aryl CH Bonds with Aryl Boronic Acids via Pd Catalysis Directed by the N,N-Dimethylaminomethyl Group
Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids with high efficiency and high regioselectivity under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxida...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2015-04, Vol.10 (4), p.840-843 |
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| container_title | Chemistry, an Asian journal |
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| creator | Zhang, Ji-Cheng Shi, Jiang-Ling Wang, Bi-Qin Hu, Ping Zhao, Ke-Qing Shi, Zhang-Jie |
| description | Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids with high efficiency and high regioselectivity under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or ‐diarylated arenes in moderate to good yields under mild conditions.
Getting the skeleton right: Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or ‐diarylated arenes in moderate to good yields under mild conditions. |
| doi_str_mv | 10.1002/asia.201403292 |
| format | Article |
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Getting the skeleton right: Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or ‐diarylated arenes in moderate to good yields under mild conditions.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.201403292</identifier><identifier>PMID: 25605476</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>biaryls ; boronic acid ; Boronic Acids - chemistry ; Catalysis ; CH activation ; Hydrocarbons - chemistry ; Hydrogen Bonding ; Molecular Structure ; N,N‐dimethylbenzylamine ; N-dimethylbenzylamine ; Oxidation-Reduction ; oxidative coupling ; Palladium - chemistry</subject><ispartof>Chemistry, an Asian journal, 2015-04, Vol.10 (4), p.840-843</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4902-16de10690ed32eb5cf22bc4eec4a2581ef0bae596454cdac02a49fc90053141a3</citedby><cites>FETCH-LOGICAL-c4902-16de10690ed32eb5cf22bc4eec4a2581ef0bae596454cdac02a49fc90053141a3</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%2Fasia.201403292$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.201403292$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27915,27916,45565,45566</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25605476$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Ji-Cheng</creatorcontrib><creatorcontrib>Shi, Jiang-Ling</creatorcontrib><creatorcontrib>Wang, Bi-Qin</creatorcontrib><creatorcontrib>Hu, Ping</creatorcontrib><creatorcontrib>Zhao, Ke-Qing</creatorcontrib><creatorcontrib>Shi, Zhang-Jie</creatorcontrib><title>Direct Oxidative Arylation of Aryl CH Bonds with Aryl Boronic Acids via Pd Catalysis Directed by the N,N-Dimethylaminomethyl Group</title><title>Chemistry, an Asian journal</title><addtitle>Chem. Asian J</addtitle><description>Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids with high efficiency and high regioselectivity under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or ‐diarylated arenes in moderate to good yields under mild conditions.
Getting the skeleton right: Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or ‐diarylated arenes in moderate to good yields under mild conditions.</description><subject>biaryls</subject><subject>boronic acid</subject><subject>Boronic Acids - chemistry</subject><subject>Catalysis</subject><subject>CH activation</subject><subject>Hydrocarbons - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Molecular Structure</subject><subject>N,N‐dimethylbenzylamine</subject><subject>N-dimethylbenzylamine</subject><subject>Oxidation-Reduction</subject><subject>oxidative coupling</subject><subject>Palladium - chemistry</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM1S2zAUhTUdOuWvW5aMlixwKsmyEi9NgECbCT9tB3YaWb6eCGwrSA7BD9An6YP0kfoKFTVk2LG659455xvpILRHyYASwr4ob9SAEcpJzFL2AW3RkaARH9LbjbVmo0207f0dIQkj6egT2mSJIAkfii3069g40C2-eDKFas0j4Mx1VVC2wbb8v-Dx399_zvCRbQqPV6ad99cj62xjNM60CfdHo_BlgceqVVXnjcc9Fwqcd7idA54dzqJjU0M7D_jaNLaXeOLscrGLPpaq8vD5Ze6gn6cnP8Zn0fRicj7OppHmKWERFQVQIlICRcwgT3TJWK45gOaKJSMKJckVJKngCdeF0oQpnpY6DR-PKacq3kEHPXfh7MMSfCtr4zVUlWrALr2kQgxjLkKXwTrordpZ7x2UcuFMrVwnKZHP1cvn6uW6-hDYf2Ev8xqKtf2162BIe8PKVNC9g5PZ9_PsLTzqs8a38LTOKncvw4uHibyZTeS3a3ol2C2VX-N_62ahNA</recordid><startdate>201504</startdate><enddate>201504</enddate><creator>Zhang, Ji-Cheng</creator><creator>Shi, Jiang-Ling</creator><creator>Wang, Bi-Qin</creator><creator>Hu, Ping</creator><creator>Zhao, Ke-Qing</creator><creator>Shi, Zhang-Jie</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</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>7X8</scope></search><sort><creationdate>201504</creationdate><title>Direct Oxidative Arylation of Aryl CH Bonds with Aryl Boronic Acids via Pd Catalysis Directed by the N,N-Dimethylaminomethyl Group</title><author>Zhang, Ji-Cheng ; Shi, Jiang-Ling ; Wang, Bi-Qin ; Hu, Ping ; Zhao, Ke-Qing ; Shi, Zhang-Jie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4902-16de10690ed32eb5cf22bc4eec4a2581ef0bae596454cdac02a49fc90053141a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>biaryls</topic><topic>boronic acid</topic><topic>Boronic Acids - chemistry</topic><topic>Catalysis</topic><topic>CH activation</topic><topic>Hydrocarbons - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Molecular Structure</topic><topic>N,N‐dimethylbenzylamine</topic><topic>N-dimethylbenzylamine</topic><topic>Oxidation-Reduction</topic><topic>oxidative coupling</topic><topic>Palladium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Ji-Cheng</creatorcontrib><creatorcontrib>Shi, Jiang-Ling</creatorcontrib><creatorcontrib>Wang, Bi-Qin</creatorcontrib><creatorcontrib>Hu, Ping</creatorcontrib><creatorcontrib>Zhao, Ke-Qing</creatorcontrib><creatorcontrib>Shi, Zhang-Jie</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>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Ji-Cheng</au><au>Shi, Jiang-Ling</au><au>Wang, Bi-Qin</au><au>Hu, Ping</au><au>Zhao, Ke-Qing</au><au>Shi, Zhang-Jie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Oxidative Arylation of Aryl CH Bonds with Aryl Boronic Acids via Pd Catalysis Directed by the N,N-Dimethylaminomethyl Group</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chem. Asian J</addtitle><date>2015-04</date><risdate>2015</risdate><volume>10</volume><issue>4</issue><spage>840</spage><epage>843</epage><pages>840-843</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids with high efficiency and high regioselectivity under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or ‐diarylated arenes in moderate to good yields under mild conditions.
Getting the skeleton right: Biaryl skeletons were directly constructed via palladium‐catalyzed ortho‐arylation of N,N‐dimethyl benzylamine with aryl boronic acids under open‐flask conditions. The N,N‐dimethylaminomethyl group was first applied as a directing group in such an oxidative coupling. Various substrates proved to be efficient coupling partners, furnishing the corresponding ortho‐monoarylated or ‐diarylated arenes in moderate to good yields under mild conditions.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25605476</pmid><doi>10.1002/asia.201403292</doi><tpages>4</tpages></addata></record> |
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| ispartof | Chemistry, an Asian journal, 2015-04, Vol.10 (4), p.840-843 |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | biaryls boronic acid Boronic Acids - chemistry Catalysis CH activation Hydrocarbons - chemistry Hydrogen Bonding Molecular Structure N,N‐dimethylbenzylamine N-dimethylbenzylamine Oxidation-Reduction oxidative coupling Palladium - chemistry |
| title | Direct Oxidative Arylation of Aryl CH Bonds with Aryl Boronic Acids via Pd Catalysis Directed by the N,N-Dimethylaminomethyl Group |
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