Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone
Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reaction...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-01, Vol.53 (3), p.742-746 |
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| creator | Nambo, Masakazu Crudden, Cathleen M. |
| description | Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane‐based materials and pharmaceuticals.
Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation. |
| doi_str_mv | 10.1002/anie.201307019 |
| format | Article |
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Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201307019</identifier><identifier>PMID: 24307286</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Aromatic compounds ; Boronic Acids - chemistry ; Carbon - chemistry ; Catalysis ; CH activation ; Detection ; Dimethyl Sulfoxide - chemistry ; Hydrogen - chemistry ; Methane - analogs & derivatives ; Methane - chemistry ; Modular ; N-heterocyclic carbenes ; palladium ; Palladium - chemistry ; Pharmaceuticals ; Phenyls ; Sulfones ; Sulfones - chemistry ; Suzuki-Miyaura coupling ; Synthesis</subject><ispartof>Angewandte Chemie International Edition, 2014-01, Vol.53 (3), p.742-746</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5479-94e70f741f0f5af097a9e7e9989e534ef95b7d8fa95df665aca415779af5524d3</citedby><cites>FETCH-LOGICAL-c5479-94e70f741f0f5af097a9e7e9989e534ef95b7d8fa95df665aca415779af5524d3</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.201307019$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201307019$$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/24307286$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nambo, Masakazu</creatorcontrib><creatorcontrib>Crudden, Cathleen M.</creatorcontrib><title>Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane‐based materials and pharmaceuticals.
Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Aromatic compounds</subject><subject>Boronic Acids - chemistry</subject><subject>Carbon - chemistry</subject><subject>Catalysis</subject><subject>CH activation</subject><subject>Detection</subject><subject>Dimethyl Sulfoxide - chemistry</subject><subject>Hydrogen - chemistry</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Modular</subject><subject>N-heterocyclic carbenes</subject><subject>palladium</subject><subject>Palladium - chemistry</subject><subject>Pharmaceuticals</subject><subject>Phenyls</subject><subject>Sulfones</subject><subject>Sulfones - chemistry</subject><subject>Suzuki-Miyaura coupling</subject><subject>Synthesis</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9v0zAYhi0E2sbYlSOKxIVLih3bcXysqtH96EalFpWb5TWfiYfjbHaiEf56XHVUiMtOnw_P--jz9yL0nuAJwbj4rL2FSYEJxQIT-QqdEF6QnApBX6c3ozQXFSfH6G2M94mvKlweoeOCJb6oyhPkb7p6cDpkq9H3DUQbs85k62B1GF0LfaM9xKxvQjf8aLKldk7Xdmjzme61G39Dna3gcQDfW-2yacro3nZ-57hJ4dFlywZ8GqvBmc7DO_TGaBfh7Hmeom9fztezi3zxdX45my7yLWdC5pKBwEYwYrDh2mAptAQBUlYSOGVgJL8TdWW05LUpS663mhEuhNSG84LV9BR92nsfQpfWi71qbdxC2t5DN0RF0rUI4aUoX0aZxILJqqIJ_fgfet8NwaePJEpwLCVmRaIme2obuhgDGPUQbJvuqQhWu9LUrjR1KC0FPjxrh7sW6gP-t6UEyD3wZB2ML-jU9Pby_F95vs_a2MOvQ1aHn6oUVHC1uZ2r5dX1fLPYrNV3-gd_AbN9</recordid><startdate>20140113</startdate><enddate>20140113</enddate><creator>Nambo, Masakazu</creator><creator>Crudden, Cathleen M.</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><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140113</creationdate><title>Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone</title><author>Nambo, Masakazu ; Crudden, Cathleen M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5479-94e70f741f0f5af097a9e7e9989e534ef95b7d8fa95df665aca415779af5524d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Aromatic compounds</topic><topic>Boronic Acids - chemistry</topic><topic>Carbon - chemistry</topic><topic>Catalysis</topic><topic>CH activation</topic><topic>Detection</topic><topic>Dimethyl Sulfoxide - chemistry</topic><topic>Hydrogen - chemistry</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Modular</topic><topic>N-heterocyclic carbenes</topic><topic>palladium</topic><topic>Palladium - chemistry</topic><topic>Pharmaceuticals</topic><topic>Phenyls</topic><topic>Sulfones</topic><topic>Sulfones - chemistry</topic><topic>Suzuki-Miyaura coupling</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nambo, Masakazu</creatorcontrib><creatorcontrib>Crudden, Cathleen M.</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><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nambo, Masakazu</au><au>Crudden, Cathleen M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-01-13</date><risdate>2014</risdate><volume>53</volume><issue>3</issue><spage>742</spage><epage>746</epage><pages>742-746</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane‐based materials and pharmaceuticals.
Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium‐catalyzed CH arylation reactions, followed by an arylative desulfonation.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24307286</pmid><doi>10.1002/anie.201307019</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Aromatic compounds Boronic Acids - chemistry Carbon - chemistry Catalysis CH activation Detection Dimethyl Sulfoxide - chemistry Hydrogen - chemistry Methane - analogs & derivatives Methane - chemistry Modular N-heterocyclic carbenes palladium Palladium - chemistry Pharmaceuticals Phenyls Sulfones Sulfones - chemistry Suzuki-Miyaura coupling Synthesis |
| title | Modular Synthesis of Triarylmethanes through Palladium-Catalyzed Sequential Arylation of Methyl Phenyl Sulfone |
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