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Palladium-catalyzed regioselective synthesis of 2(2′-biphenyl)benzimidazoles through C–H activation
An efficient palladium-catalyzed strategy through C–H bond activation for the synthesis of 2(2 ′ -biphenyl)-benzimidazoles is reported herein. The regioselective C–C bond formation proceeds in a sealed tube via oxidative C–H activation of ortho -directed 2-aryl-benzimidazole to couple with various i...
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| Published in: | Molecular diversity 2013-11, Vol.17 (4), p.641-649 |
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| Main Authors: | , , , |
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| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c372t-eeb01c42e4da500910f604486bc192584c6a76d7d0375709de8a8e8c09f320a3 |
| container_end_page | 649 |
| container_issue | 4 |
| container_start_page | 641 |
| container_title | Molecular diversity |
| container_volume | 17 |
| creator | Chen, Li-Hsun Wu, Tz-Yi Paike, Vijaykumar Sun, Chung-Ming |
| description | An efficient palladium-catalyzed strategy through C–H bond activation for the synthesis of 2(2
′
-biphenyl)-benzimidazoles is reported herein. The regioselective C–C bond formation proceeds in a sealed tube
via
oxidative C–H activation of
ortho
-directed 2-aryl-benzimidazole to couple with various iodobenzene analogs in high yields. This arylation exhibited high regioselectivity which is able to increase molecular diversity in difficult functionalized positions of parent molecules. This strategy provides a convenient and simple synthesis of biphenyl heterocyclic compounds with high regioselectivity.
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| doi_str_mv | 10.1007/s11030-013-9460-z |
| format | article |
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′
-biphenyl)-benzimidazoles is reported herein. The regioselective C–C bond formation proceeds in a sealed tube
via
oxidative C–H activation of
ortho
-directed 2-aryl-benzimidazole to couple with various iodobenzene analogs in high yields. This arylation exhibited high regioselectivity which is able to increase molecular diversity in difficult functionalized positions of parent molecules. This strategy provides a convenient and simple synthesis of biphenyl heterocyclic compounds with high regioselectivity.
Graphical Abstract</description><identifier>ISSN: 1381-1991</identifier><identifier>EISSN: 1573-501X</identifier><identifier>DOI: 10.1007/s11030-013-9460-z</identifier><identifier>PMID: 23868183</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Benzimidazoles - chemical synthesis ; Biocatalysts ; Biochemistry ; Biomedical and Life Sciences ; Biomedical research ; Catalysis ; Full-Length Paper ; Life Sciences ; Molecular Structure ; Natural products ; Nuclear Magnetic Resonance, Biomolecular ; Organic Chemistry ; Palladium - chemistry ; Pharmacy ; Polymer Sciences ; Studies</subject><ispartof>Molecular diversity, 2013-11, Vol.17 (4), p.641-649</ispartof><rights>Springer Science+Business Media Dordrecht 2013</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c372t-eeb01c42e4da500910f604486bc192584c6a76d7d0375709de8a8e8c09f320a3</citedby><cites>FETCH-LOGICAL-c372t-eeb01c42e4da500910f604486bc192584c6a76d7d0375709de8a8e8c09f320a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23868183$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Li-Hsun</creatorcontrib><creatorcontrib>Wu, Tz-Yi</creatorcontrib><creatorcontrib>Paike, Vijaykumar</creatorcontrib><creatorcontrib>Sun, Chung-Ming</creatorcontrib><title>Palladium-catalyzed regioselective synthesis of 2(2′-biphenyl)benzimidazoles through C–H activation</title><title>Molecular diversity</title><addtitle>Mol Divers</addtitle><addtitle>Mol Divers</addtitle><description>An efficient palladium-catalyzed strategy through C–H bond activation for the synthesis of 2(2
′
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via
oxidative C–H activation of
ortho
-directed 2-aryl-benzimidazole to couple with various iodobenzene analogs in high yields. This arylation exhibited high regioselectivity which is able to increase molecular diversity in difficult functionalized positions of parent molecules. This strategy provides a convenient and simple synthesis of biphenyl heterocyclic compounds with high regioselectivity.
Graphical Abstract</description><subject>Benzimidazoles - chemical synthesis</subject><subject>Biocatalysts</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedical research</subject><subject>Catalysis</subject><subject>Full-Length Paper</subject><subject>Life Sciences</subject><subject>Molecular Structure</subject><subject>Natural products</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Organic Chemistry</subject><subject>Palladium - chemistry</subject><subject>Pharmacy</subject><subject>Polymer Sciences</subject><subject>Studies</subject><issn>1381-1991</issn><issn>1573-501X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp1kc1u1DAUhS0EoqXwAGxQJDbtwnD9E9tZohFtkSqVRRfsLMe5mXGVxEOcVJqs-g68SR-pT1KPpiCExOpaut85ts8h5D2DTwxAf06MgQAKTNBKKqDLC3LMSi1oCezHy3wWhlFWVeyIvEnpFiCrmHhNjrgwyjAjjsn6u-s614S5p95Nrtst2BQjrkNM2KGfwh0WaTdMG0whFbEt-Cl_vH-gddhucNh1ZzUOS-hD45bYYSqmzRjn9aZYPd7_uizc3sBNIQ5vyavWdQnfPc8TcnP-9WZ1Sa-uL76tvlxRLzSfKGINzEuOsnElQMWgVSClUbVnFS-N9Mpp1egGhC41VA0aZ9B4qFrBwYkTcnqw3Y7x54xpsn1IHvMXB4xzskxKIbnU2mT04z_obZzHIT8uU8oYpTjwTLED5ceY0oit3Y6hd-POMrD7EuyhBJuDtfsS7JI1H56d57rH5o_id-oZ4Acg5dWwxvGvq__r-gTWh5SW</recordid><startdate>20131101</startdate><enddate>20131101</enddate><creator>Chen, Li-Hsun</creator><creator>Wu, Tz-Yi</creator><creator>Paike, Vijaykumar</creator><creator>Sun, Chung-Ming</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>20131101</creationdate><title>Palladium-catalyzed regioselective synthesis of 2(2′-biphenyl)benzimidazoles through C–H activation</title><author>Chen, Li-Hsun ; 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′
-biphenyl)-benzimidazoles is reported herein. The regioselective C–C bond formation proceeds in a sealed tube
via
oxidative C–H activation of
ortho
-directed 2-aryl-benzimidazole to couple with various iodobenzene analogs in high yields. This arylation exhibited high regioselectivity which is able to increase molecular diversity in difficult functionalized positions of parent molecules. This strategy provides a convenient and simple synthesis of biphenyl heterocyclic compounds with high regioselectivity.
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| ispartof | Molecular diversity, 2013-11, Vol.17 (4), p.641-649 |
| issn | 1381-1991 1573-501X |
| language | eng |
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| subjects | Benzimidazoles - chemical synthesis Biocatalysts Biochemistry Biomedical and Life Sciences Biomedical research Catalysis Full-Length Paper Life Sciences Molecular Structure Natural products Nuclear Magnetic Resonance, Biomolecular Organic Chemistry Palladium - chemistry Pharmacy Polymer Sciences Studies |
| title | Palladium-catalyzed regioselective synthesis of 2(2′-biphenyl)benzimidazoles through C–H activation |
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