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Ruthenium(η⁶,η¹-arene-CH₂-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water
A series of new benzimidazolium halides were synthesized in good yields as unsymmetrical -heterocyclic carbene (NHC) precursors containing the N-CH₂-arene group. The benzimidazolium halides were readily converted into ruthenium(II)-NHC complexes with the general formula [RuCl₂(η⁶,η¹-arene-CH₂-NHC)]....
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| Published in: | Molecules (Basel, Switzerland) Switzerland), 2018-03, Vol.23 (3), p.647 |
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| creator | Kaloğlu, Nazan Özdemir, İsmail Gürbüz, Nevin Arslan, Hakan Dixneuf, Pierre H |
| description | A series of new benzimidazolium halides were synthesized in good yields as unsymmetrical
-heterocyclic carbene (NHC) precursors containing the N-CH₂-arene group. The benzimidazolium halides were readily converted into ruthenium(II)-NHC complexes with the general formula [RuCl₂(η⁶,η¹-arene-CH₂-NHC)]. The structures of all new compounds were characterized by ¹H NMR (Nuclear Magnetic Resonance),
C NMR, FT-IR (Fourier Transform Infrared) spectroscopy and elemental analysis techniques. The single crystal structure of one benzimidazole ruthenium complex,
, was determined. The complex is best thought of as containing an octahedrally coordinated Ru center with the arene residue occupying three sites, the remaining sites being occupied by a (carbene)C-Ru bond and two Ru-Cl bonds. The catalytic activity of [RuCl₂(η⁶,η
-arene-CH₂-NHC)] complexes was evaluated in the direct (hetero)arylation of 2-phenylpyridine with (hetero)aryl chlorides in water as the nontoxic reaction medium. These results show that catalysts
and
were the best for monoarylation with simple phenyl and tolyl chlorides. For functional aryl chlorides,
,
, and
appeared to be the most efficient. |
| doi_str_mv | 10.3390/molecules23030647 |
| format | article |
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-heterocyclic carbene (NHC) precursors containing the N-CH₂-arene group. The benzimidazolium halides were readily converted into ruthenium(II)-NHC complexes with the general formula [RuCl₂(η⁶,η¹-arene-CH₂-NHC)]. The structures of all new compounds were characterized by ¹H NMR (Nuclear Magnetic Resonance),
C NMR, FT-IR (Fourier Transform Infrared) spectroscopy and elemental analysis techniques. The single crystal structure of one benzimidazole ruthenium complex,
, was determined. The complex is best thought of as containing an octahedrally coordinated Ru center with the arene residue occupying three sites, the remaining sites being occupied by a (carbene)C-Ru bond and two Ru-Cl bonds. The catalytic activity of [RuCl₂(η⁶,η
-arene-CH₂-NHC)] complexes was evaluated in the direct (hetero)arylation of 2-phenylpyridine with (hetero)aryl chlorides in water as the nontoxic reaction medium. These results show that catalysts
and
were the best for monoarylation with simple phenyl and tolyl chlorides. For functional aryl chlorides,
,
, and
appeared to be the most efficient.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules23030647</identifier><identifier>PMID: 29534012</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>2-phenylpyridine ; Acids, Heterocyclic - chemistry ; Aromatic compounds ; Benzimidazoles ; Catalysis ; Catalysts ; Catalytic activity ; Chemical Sciences ; Chlorides ; Chlorides - chemistry ; Crystal structure ; Crystallography, X-Ray ; direct arylation ; Fourier transforms ; Halides ; homogeneous catalysis ; Infrared analysis ; Infrared spectroscopy ; Magnetic Resonance Spectroscopy ; Models, Molecular ; Molecular Structure ; N-heterocyclic carbene ; NMR ; Nuclear magnetic resonance ; Organometallic Compounds - chemistry ; Pyridines - chemistry ; Ruthenium ; Ruthenium - chemistry ; Ruthenium compounds ; single crystal structure ; Single crystals ; Spectroscopy, Fourier Transform Infrared ; Water - chemistry</subject><ispartof>Molecules (Basel, Switzerland), 2018-03, Vol.23 (3), p.647</ispartof><rights>2018. This work is licensed under https://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><rights>2018 by the authors. 2018</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c597t-d8973e0dff1afe262ce4350a4fe106010ca2dfecebd17f2705dd7df898493d53</citedby><cites>FETCH-LOGICAL-c597t-d8973e0dff1afe262ce4350a4fe106010ca2dfecebd17f2705dd7df898493d53</cites><orcidid>0000-0001-6325-0216 ; 0000-0003-0046-9442 ; 0000-0003-3201-3597 ; 0000-0002-3025-6969</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2108555803/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2108555803?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,74998</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29534012$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://univ-rennes.hal.science/hal-01744295$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Kaloğlu, Nazan</creatorcontrib><creatorcontrib>Özdemir, İsmail</creatorcontrib><creatorcontrib>Gürbüz, Nevin</creatorcontrib><creatorcontrib>Arslan, Hakan</creatorcontrib><creatorcontrib>Dixneuf, Pierre H</creatorcontrib><title>Ruthenium(η⁶,η¹-arene-CH₂-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>A series of new benzimidazolium halides were synthesized in good yields as unsymmetrical
-heterocyclic carbene (NHC) precursors containing the N-CH₂-arene group. The benzimidazolium halides were readily converted into ruthenium(II)-NHC complexes with the general formula [RuCl₂(η⁶,η¹-arene-CH₂-NHC)]. The structures of all new compounds were characterized by ¹H NMR (Nuclear Magnetic Resonance),
C NMR, FT-IR (Fourier Transform Infrared) spectroscopy and elemental analysis techniques. The single crystal structure of one benzimidazole ruthenium complex,
, was determined. The complex is best thought of as containing an octahedrally coordinated Ru center with the arene residue occupying three sites, the remaining sites being occupied by a (carbene)C-Ru bond and two Ru-Cl bonds. The catalytic activity of [RuCl₂(η⁶,η
-arene-CH₂-NHC)] complexes was evaluated in the direct (hetero)arylation of 2-phenylpyridine with (hetero)aryl chlorides in water as the nontoxic reaction medium. These results show that catalysts
and
were the best for monoarylation with simple phenyl and tolyl chlorides. For functional aryl chlorides,
,
, and
appeared to be the most efficient.</description><subject>2-phenylpyridine</subject><subject>Acids, Heterocyclic - chemistry</subject><subject>Aromatic compounds</subject><subject>Benzimidazoles</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Catalytic activity</subject><subject>Chemical Sciences</subject><subject>Chlorides</subject><subject>Chlorides - chemistry</subject><subject>Crystal structure</subject><subject>Crystallography, X-Ray</subject><subject>direct arylation</subject><subject>Fourier transforms</subject><subject>Halides</subject><subject>homogeneous catalysis</subject><subject>Infrared analysis</subject><subject>Infrared spectroscopy</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>N-heterocyclic carbene</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organometallic Compounds - chemistry</subject><subject>Pyridines - chemistry</subject><subject>Ruthenium</subject><subject>Ruthenium - chemistry</subject><subject>Ruthenium compounds</subject><subject>single crystal structure</subject><subject>Single crystals</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Water - chemistry</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNplks1uEzEQx1cIREvhAbiglbgkEgtjez8vSNHykUoRIFSJo-XY48bRZp3a3qIcONCHouLKA_Qh-iQ4TanacrI185_ff8aeJHlO4DVjDbxZ2Q7l0KGnDBiUefUg2Sc5hYxB3jy8dd9Lnni_BKAkJ8XjZI82BcuB0P3kx9chLLA3w2p0cX7589eri_M_vzPhsMesnV6enWWfpu04bUUQ3cYHn2rr0nfGoQzpxG06EYztU6tTmn2JnE233jijTI_pdxMW6WiKAZ0db6Vpu-hsTKJPTZ9-EzHxNHmkRefx2fV5kBx9eH_UTrPZ54-H7WSWyaKpQqbqpmIISmsiNNKSSsxZASLXSKAEAlJQpVHiXJFK0woKpSql66bOG6YKdpAc7rDKiiVfO7MSbsOtMPwqYN0xFy4Y2SEHASVCtGKizOcC60bNFRa0xIpoUDKy3u5Y62G-QiWxD050d6B3M71Z8GN7ymOfFQCLgPEOsLhXNp3M-DYWdXkef-iURO3o2szZkwF94CvjJXad6NEOnlMgrKqLsmyi9OU96dIOro-vyimBuiiK-sqc7FTSWe8d6psOCPDtTvH_dirWvLg98U3FvyVifwGZI86R</recordid><startdate>20180313</startdate><enddate>20180313</enddate><creator>Kaloğlu, Nazan</creator><creator>Özdemir, İsmail</creator><creator>Gürbüz, Nevin</creator><creator>Arslan, Hakan</creator><creator>Dixneuf, Pierre H</creator><general>MDPI AG</general><general>MDPI</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>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>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-6325-0216</orcidid><orcidid>https://orcid.org/0000-0003-0046-9442</orcidid><orcidid>https://orcid.org/0000-0003-3201-3597</orcidid><orcidid>https://orcid.org/0000-0002-3025-6969</orcidid></search><sort><creationdate>20180313</creationdate><title>Ruthenium(η⁶,η¹-arene-CH₂-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water</title><author>Kaloğlu, Nazan ; Özdemir, İsmail ; Gürbüz, Nevin ; Arslan, Hakan ; Dixneuf, Pierre H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c597t-d8973e0dff1afe262ce4350a4fe106010ca2dfecebd17f2705dd7df898493d53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>2-phenylpyridine</topic><topic>Acids, Heterocyclic - chemistry</topic><topic>Aromatic compounds</topic><topic>Benzimidazoles</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Catalytic activity</topic><topic>Chemical Sciences</topic><topic>Chlorides</topic><topic>Chlorides - chemistry</topic><topic>Crystal structure</topic><topic>Crystallography, X-Ray</topic><topic>direct arylation</topic><topic>Fourier transforms</topic><topic>Halides</topic><topic>homogeneous catalysis</topic><topic>Infrared analysis</topic><topic>Infrared spectroscopy</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>N-heterocyclic carbene</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organometallic Compounds - chemistry</topic><topic>Pyridines - chemistry</topic><topic>Ruthenium</topic><topic>Ruthenium - chemistry</topic><topic>Ruthenium compounds</topic><topic>single crystal structure</topic><topic>Single crystals</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaloğlu, Nazan</creatorcontrib><creatorcontrib>Özdemir, İsmail</creatorcontrib><creatorcontrib>Gürbüz, Nevin</creatorcontrib><creatorcontrib>Arslan, Hakan</creatorcontrib><creatorcontrib>Dixneuf, Pierre H</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content (ProQuest)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaloğlu, Nazan</au><au>Özdemir, İsmail</au><au>Gürbüz, Nevin</au><au>Arslan, Hakan</au><au>Dixneuf, Pierre H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ruthenium(η⁶,η¹-arene-CH₂-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2018-03-13</date><risdate>2018</risdate><volume>23</volume><issue>3</issue><spage>647</spage><pages>647-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>A series of new benzimidazolium halides were synthesized in good yields as unsymmetrical
-heterocyclic carbene (NHC) precursors containing the N-CH₂-arene group. The benzimidazolium halides were readily converted into ruthenium(II)-NHC complexes with the general formula [RuCl₂(η⁶,η¹-arene-CH₂-NHC)]. The structures of all new compounds were characterized by ¹H NMR (Nuclear Magnetic Resonance),
C NMR, FT-IR (Fourier Transform Infrared) spectroscopy and elemental analysis techniques. The single crystal structure of one benzimidazole ruthenium complex,
, was determined. The complex is best thought of as containing an octahedrally coordinated Ru center with the arene residue occupying three sites, the remaining sites being occupied by a (carbene)C-Ru bond and two Ru-Cl bonds. The catalytic activity of [RuCl₂(η⁶,η
-arene-CH₂-NHC)] complexes was evaluated in the direct (hetero)arylation of 2-phenylpyridine with (hetero)aryl chlorides in water as the nontoxic reaction medium. These results show that catalysts
and
were the best for monoarylation with simple phenyl and tolyl chlorides. For functional aryl chlorides,
,
, and
appeared to be the most efficient.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>29534012</pmid><doi>10.3390/molecules23030647</doi><orcidid>https://orcid.org/0000-0001-6325-0216</orcidid><orcidid>https://orcid.org/0000-0003-0046-9442</orcidid><orcidid>https://orcid.org/0000-0003-3201-3597</orcidid><orcidid>https://orcid.org/0000-0002-3025-6969</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Molecules (Basel, Switzerland), 2018-03, Vol.23 (3), p.647 |
| issn | 1420-3049 1420-3049 |
| language | eng |
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| source | Publicly Available Content (ProQuest); PubMed Central |
| subjects | 2-phenylpyridine Acids, Heterocyclic - chemistry Aromatic compounds Benzimidazoles Catalysis Catalysts Catalytic activity Chemical Sciences Chlorides Chlorides - chemistry Crystal structure Crystallography, X-Ray direct arylation Fourier transforms Halides homogeneous catalysis Infrared analysis Infrared spectroscopy Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure N-heterocyclic carbene NMR Nuclear magnetic resonance Organometallic Compounds - chemistry Pyridines - chemistry Ruthenium Ruthenium - chemistry Ruthenium compounds single crystal structure Single crystals Spectroscopy, Fourier Transform Infrared Water - chemistry |
| title | Ruthenium(η⁶,η¹-arene-CH₂-NHC) Catalysts for Direct Arylation of 2-Phenylpyridine with (Hetero)Aryl Chlorides in Water |
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