An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations
C−H activation is a versatile tool for appending aryl groups to aromatic systems. However, heavy demands on multiple catalytic cycle operations and site‐selectivity have limited its use for graphene segment synthesis. A Pd‐catal‐ yzed one‐step synthesis of functionalized triphenylene frameworks is d...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-04, Vol.56 (18), p.5007-5011 |
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| creator | Mathew, Bijoy P. Yang, Hyun Ji Kim, Joohee Lee, Jae Bin Kim, Yun‐Tae Lee, Sungmin Lee, Chang Young Choe, Wonyoung Myung, Kyungjae Park, Jang‐Ung Hong, Sung You |
| description | C−H activation is a versatile tool for appending aryl groups to aromatic systems. However, heavy demands on multiple catalytic cycle operations and site‐selectivity have limited its use for graphene segment synthesis. A Pd‐catal‐ yzed one‐step synthesis of functionalized triphenylene frameworks is disclosed, which proceeds by 2‐ or 4‐fold C−H arylation of unactivated benzene derivatives. A Pd2(dibenzylideneacetone)3 catalytic system, using cyclic diaryliodonium salts as π‐extending agents, leads to site‐selective inter‐ and intramolecular tandem arylation sequences. Moreover, N‐substituted triphenylenes are applied to a field‐effect transistor sensor for rapid, sensitive, and reversible alcohol vapor detection.
Closing the circle: Palladium‐catalyzed 2‐ or 4‐fold C−H arylation of unactivated arenes was developed to access substituted triphenylene frameworks. |
| doi_str_mv | 10.1002/anie.201700405 |
| format | Article |
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Closing the circle: Palladium‐catalyzed 2‐ or 4‐fold C−H arylation of unactivated arenes was developed to access substituted triphenylene frameworks.</description><subject>Activation</subject><subject>Alcohols</subject><subject>Aromatic compounds</subject><subject>arylation</subject><subject>Benzene</subject><subject>Buildings</subject><subject>Catalysis</subject><subject>C−H activation</subject><subject>Derivatives</subject><subject>diaryliodonium salt</subject><subject>Field effect transistors</subject><subject>Graphene</subject><subject>Nucleotide sequence</subject><subject>palladium</subject><subject>Salts</subject><subject>Selectivity</subject><subject>Strategy</subject><subject>triphenylene</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkcFuFSEUhonR2FrdujQkbtzMFQYYmOX0prVNqi5a14RhDr1ULnOFmTbzBq59RJ9Emltr4kLPhrP4_i_Aj9BrSlaUkPq9iR5WNaGSEE7EE3RIRU0rJiV7WnbOWCWVoAfoRc43hVeKNM_RQa2YpKQhh2jTRdzFOAcz-VvAl0ucNjB5iy-nZCa4XrAbEz6efRh8vMZXye82EJcAEfBpMlu4G9PXjPsFf5zD5HcB8Prn9x9n-HiMA-5ssRbzGPNL9MyZkOHVw3mEvpyeXK3PqovPH87X3UVlBeGisoNkjDJiaycBDDfK8r4fWtkbLnthBWvKexgVdmiUchac42IwTpYcMY6xI_Ru792l8dsMedJbny2EYCKMc9ZUKV5-q25lQd_-hd6Mc4rldpq2REgm26b9J6XKiJZxXqjVnrJpzDmB07vktyYtmhJ935S-b0o_NlUCbx60c7-F4RH_XU0B2j1w5wMs_9Hp7tP5yR_5L7pVoGc</recordid><startdate>20170424</startdate><enddate>20170424</enddate><creator>Mathew, Bijoy P.</creator><creator>Yang, Hyun Ji</creator><creator>Kim, Joohee</creator><creator>Lee, Jae Bin</creator><creator>Kim, Yun‐Tae</creator><creator>Lee, Sungmin</creator><creator>Lee, Chang Young</creator><creator>Choe, Wonyoung</creator><creator>Myung, Kyungjae</creator><creator>Park, Jang‐Ung</creator><creator>Hong, Sung You</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5500-2298</orcidid><orcidid>https://orcid.org/0000-0002-5785-4475</orcidid><orcidid>https://orcid.org/0000-0002-8245-0990</orcidid><orcidid>https://orcid.org/0000-0002-0013-9489</orcidid><orcidid>https://orcid.org/0000-0003-0957-1187</orcidid><orcidid>https://orcid.org/0000-0002-0294-9565</orcidid><orcidid>https://orcid.org/0000-0001-7975-6190</orcidid><orcidid>https://orcid.org/0000-0002-6060-4936</orcidid><orcidid>https://orcid.org/0000-0002-2757-8019</orcidid><orcidid>https://orcid.org/0000-0003-1522-4958</orcidid><orcidid>https://orcid.org/0000-0002-4624-8007</orcidid></search><sort><creationdate>20170424</creationdate><title>An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations</title><author>Mathew, Bijoy P. ; Yang, Hyun Ji ; Kim, Joohee ; Lee, Jae Bin ; Kim, Yun‐Tae ; Lee, Sungmin ; Lee, Chang Young ; Choe, Wonyoung ; Myung, Kyungjae ; Park, Jang‐Ung ; Hong, Sung You</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5045-cd733130c2f7eea4a8c4bbd97ba47b5c536851315cd688fceff45daf7d730af33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Activation</topic><topic>Alcohols</topic><topic>Aromatic compounds</topic><topic>arylation</topic><topic>Benzene</topic><topic>Buildings</topic><topic>Catalysis</topic><topic>C−H activation</topic><topic>Derivatives</topic><topic>diaryliodonium salt</topic><topic>Field effect transistors</topic><topic>Graphene</topic><topic>Nucleotide sequence</topic><topic>palladium</topic><topic>Salts</topic><topic>Selectivity</topic><topic>Strategy</topic><topic>triphenylene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mathew, Bijoy P.</creatorcontrib><creatorcontrib>Yang, Hyun Ji</creatorcontrib><creatorcontrib>Kim, Joohee</creatorcontrib><creatorcontrib>Lee, Jae Bin</creatorcontrib><creatorcontrib>Kim, Yun‐Tae</creatorcontrib><creatorcontrib>Lee, Sungmin</creatorcontrib><creatorcontrib>Lee, Chang Young</creatorcontrib><creatorcontrib>Choe, Wonyoung</creatorcontrib><creatorcontrib>Myung, Kyungjae</creatorcontrib><creatorcontrib>Park, Jang‐Ung</creatorcontrib><creatorcontrib>Hong, Sung You</creatorcontrib><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>Mathew, Bijoy P.</au><au>Yang, Hyun Ji</au><au>Kim, Joohee</au><au>Lee, Jae Bin</au><au>Kim, Yun‐Tae</au><au>Lee, Sungmin</au><au>Lee, Chang Young</au><au>Choe, Wonyoung</au><au>Myung, Kyungjae</au><au>Park, Jang‐Ung</au><au>Hong, Sung You</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-04-24</date><risdate>2017</risdate><volume>56</volume><issue>18</issue><spage>5007</spage><epage>5011</epage><pages>5007-5011</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>C−H activation is a versatile tool for appending aryl groups to aromatic systems. However, heavy demands on multiple catalytic cycle operations and site‐selectivity have limited its use for graphene segment synthesis. A Pd‐catal‐ yzed one‐step synthesis of functionalized triphenylene frameworks is disclosed, which proceeds by 2‐ or 4‐fold C−H arylation of unactivated benzene derivatives. A Pd2(dibenzylideneacetone)3 catalytic system, using cyclic diaryliodonium salts as π‐extending agents, leads to site‐selective inter‐ and intramolecular tandem arylation sequences. Moreover, N‐substituted triphenylenes are applied to a field‐effect transistor sensor for rapid, sensitive, and reversible alcohol vapor detection.
Closing the circle: Palladium‐catalyzed 2‐ or 4‐fold C−H arylation of unactivated arenes was developed to access substituted triphenylene frameworks.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28371060</pmid><doi>10.1002/anie.201700405</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-5500-2298</orcidid><orcidid>https://orcid.org/0000-0002-5785-4475</orcidid><orcidid>https://orcid.org/0000-0002-8245-0990</orcidid><orcidid>https://orcid.org/0000-0002-0013-9489</orcidid><orcidid>https://orcid.org/0000-0003-0957-1187</orcidid><orcidid>https://orcid.org/0000-0002-0294-9565</orcidid><orcidid>https://orcid.org/0000-0001-7975-6190</orcidid><orcidid>https://orcid.org/0000-0002-6060-4936</orcidid><orcidid>https://orcid.org/0000-0002-2757-8019</orcidid><orcidid>https://orcid.org/0000-0003-1522-4958</orcidid><orcidid>https://orcid.org/0000-0002-4624-8007</orcidid></addata></record> |
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| subjects | Activation Alcohols Aromatic compounds arylation Benzene Buildings Catalysis C−H activation Derivatives diaryliodonium salt Field effect transistors Graphene Nucleotide sequence palladium Salts Selectivity Strategy triphenylene |
| title | An Annulative Synthetic Strategy for Building Triphenylene Frameworks by Multiple C−H Bond Activations |
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