Silver‐Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids
A practical and operationally simple protocol for the assembly of 6‐aryl‐substituted purines through the direct C6–H arylation of purines and 8‐azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the...
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| Veröffentlicht in: | European journal of organic chemistry 2017-06, Vol.2017 (24), p.3415-3420 |
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| container_title | European journal of organic chemistry |
| container_volume | 2017 |
| creator | Tian, Miao Yu, Mingwu Shi, Tingting Hu, Junbin Li, Shunlai Xu, Jiaxi Chen, Ning Du, Hongguang |
| description | A practical and operationally simple protocol for the assembly of 6‐aryl‐substituted purines through the direct C6–H arylation of purines and 8‐azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the oxidant in the presence of silver(I). The reaction was found to be regioselective with the arylation occurring predominantly at the C6 position, and a large variety of functional groups, including halides, esters, hydroxy groups, and heterocycles, were tolerated.
An efficient protocol for the direct C6–H arylation of purines and purine nucleosides is described under the catalysis of silver nitrate and under ambient conditions. A wide assortment of purines and arylboronic acids can be employed in this process to afford C6‐arylpurines and purine nucleosides with high regioselectivity. TFA = trifluoroacetic acid; DCE = 1,2‐dichloroethane. |
| doi_str_mv | 10.1002/ejoc.201700406 |
| format | Article |
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An efficient protocol for the direct C6–H arylation of purines and purine nucleosides is described under the catalysis of silver nitrate and under ambient conditions. A wide assortment of purines and arylboronic acids can be employed in this process to afford C6‐arylpurines and purine nucleosides with high regioselectivity. TFA = trifluoroacetic acid; DCE = 1,2‐dichloroethane.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201700406</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Ammonium peroxodisulfate ; Aromatic compounds ; Assembly ; Boronic acids ; C–H activation ; Esters ; Functional groups ; Halides ; Nucleosides ; Purines ; Silver</subject><ispartof>European journal of organic chemistry, 2017-06, Vol.2017 (24), p.3415-3420</ispartof><rights>2017 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3176-214e1301cce7eed5e448b84ff67ab6066d3270d08e52191db3c46f49740a80d73</citedby><cites>FETCH-LOGICAL-c3176-214e1301cce7eed5e448b84ff67ab6066d3270d08e52191db3c46f49740a80d73</cites><orcidid>0000-0002-9039-4933 ; 0000-0001-6660-4892</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201700406$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201700406$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Tian, Miao</creatorcontrib><creatorcontrib>Yu, Mingwu</creatorcontrib><creatorcontrib>Shi, Tingting</creatorcontrib><creatorcontrib>Hu, Junbin</creatorcontrib><creatorcontrib>Li, Shunlai</creatorcontrib><creatorcontrib>Xu, Jiaxi</creatorcontrib><creatorcontrib>Chen, Ning</creatorcontrib><creatorcontrib>Du, Hongguang</creatorcontrib><title>Silver‐Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids</title><title>European journal of organic chemistry</title><description>A practical and operationally simple protocol for the assembly of 6‐aryl‐substituted purines through the direct C6–H arylation of purines and 8‐azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the oxidant in the presence of silver(I). The reaction was found to be regioselective with the arylation occurring predominantly at the C6 position, and a large variety of functional groups, including halides, esters, hydroxy groups, and heterocycles, were tolerated.
An efficient protocol for the direct C6–H arylation of purines and purine nucleosides is described under the catalysis of silver nitrate and under ambient conditions. A wide assortment of purines and arylboronic acids can be employed in this process to afford C6‐arylpurines and purine nucleosides with high regioselectivity. TFA = trifluoroacetic acid; DCE = 1,2‐dichloroethane.</description><subject>Ammonium peroxodisulfate</subject><subject>Aromatic compounds</subject><subject>Assembly</subject><subject>Boronic acids</subject><subject>C–H activation</subject><subject>Esters</subject><subject>Functional groups</subject><subject>Halides</subject><subject>Nucleosides</subject><subject>Purines</subject><subject>Silver</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkF1LwzAUhoMoOKe3Xge87jxp06S5HPVjynCCCt6VNkkxozYzaR31aj9B8B_ul9i5oZdenZfD85wDL0KnBEYEIDzXcytHIRAOQIHtoQEBIQJgAvb7TCMaEBE9H6Ij7-cAIBgjAyQfTPWu3Xr1meZNXnUfWuEL47RscMrWq68JHruuyhtja2xLfN86U2uP81rtMr5rZaWtN6pfL03z8iMU1tnaSDyWRvljdFDmldcnuzlET1eXj-kkmM6ub9LxNJAR4SwICdUkAiKl5lqrWFOaFAktS8bzggFjKgo5KEh0HBJBVBFJykoqOIU8AcWjITrb3l04-9Zq32Rz27q6f5n1POUijmPSU6MtJZ313ukyWzjzmrsuI5Btisw2RWa_RfaC2ApLU-nuHzq7vJ2lf-43W3t43Q</recordid><startdate>20170630</startdate><enddate>20170630</enddate><creator>Tian, Miao</creator><creator>Yu, Mingwu</creator><creator>Shi, Tingting</creator><creator>Hu, Junbin</creator><creator>Li, Shunlai</creator><creator>Xu, Jiaxi</creator><creator>Chen, Ning</creator><creator>Du, Hongguang</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-9039-4933</orcidid><orcidid>https://orcid.org/0000-0001-6660-4892</orcidid></search><sort><creationdate>20170630</creationdate><title>Silver‐Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids</title><author>Tian, Miao ; Yu, Mingwu ; Shi, Tingting ; Hu, Junbin ; Li, Shunlai ; Xu, Jiaxi ; Chen, Ning ; Du, Hongguang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3176-214e1301cce7eed5e448b84ff67ab6066d3270d08e52191db3c46f49740a80d73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Ammonium peroxodisulfate</topic><topic>Aromatic compounds</topic><topic>Assembly</topic><topic>Boronic acids</topic><topic>C–H activation</topic><topic>Esters</topic><topic>Functional groups</topic><topic>Halides</topic><topic>Nucleosides</topic><topic>Purines</topic><topic>Silver</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tian, Miao</creatorcontrib><creatorcontrib>Yu, Mingwu</creatorcontrib><creatorcontrib>Shi, Tingting</creatorcontrib><creatorcontrib>Hu, Junbin</creatorcontrib><creatorcontrib>Li, Shunlai</creatorcontrib><creatorcontrib>Xu, Jiaxi</creatorcontrib><creatorcontrib>Chen, Ning</creatorcontrib><creatorcontrib>Du, Hongguang</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tian, Miao</au><au>Yu, Mingwu</au><au>Shi, Tingting</au><au>Hu, Junbin</au><au>Li, Shunlai</au><au>Xu, Jiaxi</au><au>Chen, Ning</au><au>Du, Hongguang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Silver‐Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids</atitle><jtitle>European journal of organic chemistry</jtitle><date>2017-06-30</date><risdate>2017</risdate><volume>2017</volume><issue>24</issue><spage>3415</spage><epage>3420</epage><pages>3415-3420</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A practical and operationally simple protocol for the assembly of 6‐aryl‐substituted purines through the direct C6–H arylation of purines and 8‐azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the oxidant in the presence of silver(I). The reaction was found to be regioselective with the arylation occurring predominantly at the C6 position, and a large variety of functional groups, including halides, esters, hydroxy groups, and heterocycles, were tolerated.
An efficient protocol for the direct C6–H arylation of purines and purine nucleosides is described under the catalysis of silver nitrate and under ambient conditions. A wide assortment of purines and arylboronic acids can be employed in this process to afford C6‐arylpurines and purine nucleosides with high regioselectivity. TFA = trifluoroacetic acid; DCE = 1,2‐dichloroethane.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201700406</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-9039-4933</orcidid><orcidid>https://orcid.org/0000-0001-6660-4892</orcidid></addata></record> |
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| subjects | Ammonium peroxodisulfate Aromatic compounds Assembly Boronic acids C–H activation Esters Functional groups Halides Nucleosides Purines Silver |
| title | Silver‐Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids |
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