Site-selectivity in TBADT-photocatalyzed C(sp3)–H Functionalization of Saturated Alcohols and Alkanes
Site-selectivity in C(sp3)–H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, C–H bond α to the hydroxy group was preferentially functionalized. The α-site-selectivity is rationalized by polar effects...
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Veröffentlicht in: | Chemistry letters 2018-01, Vol.47 (2), p.207-209 |
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creator | Fukuyama, Takahide Yamada, Keiichi Nishikawa, Tomohiro Ravelli, Davide Fagnoni, Maurizio Ryu, Illhyong |
description | Site-selectivity in C(sp3)–H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, C–H bond α to the hydroxy group was preferentially functionalized. The α-site-selectivity is rationalized by polar effects imparted by the hydroxy group in the SH2 transition states. In contrast, C–H functionalization of alkanes was largely affected by steric effects. |
doi_str_mv | 10.1246/cl.171068 |
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In contrast, C–H functionalization of alkanes was largely affected by steric effects.</description><subject>Alcohol</subject><subject>Aliphatic alcohols</subject><subject>Aliphatic compounds</subject><subject>Alkanes</subject><subject>Hydrogen bonds</subject><subject>Selectivity</subject><subject>Steric effects</subject><issn>0366-7022</issn><issn>1348-0715</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNplkL9OwzAQhy0EEqUw8AaRWOiQYsex44ylUIpUiaFljhz_oS5uHGIHKZ14B96QJyFVKzEw3Z303ae7HwDXCI5RktI7YccoQ5CyEzBAOGUxzBA5BQOIKY0zmCTn4ML7DYSQ5TgZgLelCSr2yioRzKcJXWSqaHU_eVjF9doFJ3jgttspGU1vfY1HP1_f82jWVj3tKm7Nju-byOloyUPb8NCTEyvc2lkf8Wo_vPNK-Utwprn16upYh-B19riazuPFy9PzdLKIBYFpiLnUWEIlJcmhTHHGcIlkmlNBiUQYaiJL1j9UMo60ZiqBpJSIEKgzTDSiBA_BzcFbN-6jVT4UG9c2_aW-SJIUYZIzRntqdKBE47xvlC7qxmx50xUIFvscC2GLQ449S4_sWm2N6E1OGBW6Da959Wf_v_gLtu146w</recordid><startdate>20180101</startdate><enddate>20180101</enddate><creator>Fukuyama, Takahide</creator><creator>Yamada, Keiichi</creator><creator>Nishikawa, Tomohiro</creator><creator>Ravelli, Davide</creator><creator>Fagnoni, Maurizio</creator><creator>Ryu, Illhyong</creator><general>The Chemical Society of Japan</general><general>Chemical Society of Japan</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20180101</creationdate><title>Site-selectivity in TBADT-photocatalyzed C(sp3)–H Functionalization of Saturated Alcohols and Alkanes</title><author>Fukuyama, Takahide ; Yamada, Keiichi ; Nishikawa, Tomohiro ; Ravelli, Davide ; Fagnoni, Maurizio ; Ryu, Illhyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c504t-adf3d0edd590d43783b1d496c65d130f5db8715b8a1ff8e205bd1550f735f1653</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alcohol</topic><topic>Aliphatic alcohols</topic><topic>Aliphatic compounds</topic><topic>Alkanes</topic><topic>Hydrogen bonds</topic><topic>Selectivity</topic><topic>Steric effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fukuyama, Takahide</creatorcontrib><creatorcontrib>Yamada, Keiichi</creatorcontrib><creatorcontrib>Nishikawa, Tomohiro</creatorcontrib><creatorcontrib>Ravelli, Davide</creatorcontrib><creatorcontrib>Fagnoni, Maurizio</creatorcontrib><creatorcontrib>Ryu, Illhyong</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fukuyama, Takahide</au><au>Yamada, Keiichi</au><au>Nishikawa, Tomohiro</au><au>Ravelli, Davide</au><au>Fagnoni, Maurizio</au><au>Ryu, Illhyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Site-selectivity in TBADT-photocatalyzed C(sp3)–H Functionalization of Saturated Alcohols and Alkanes</atitle><jtitle>Chemistry letters</jtitle><date>2018-01-01</date><risdate>2018</risdate><volume>47</volume><issue>2</issue><spage>207</spage><epage>209</epage><pages>207-209</pages><issn>0366-7022</issn><eissn>1348-0715</eissn><abstract>Site-selectivity in C(sp3)–H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, C–H bond α to the hydroxy group was preferentially functionalized. The α-site-selectivity is rationalized by polar effects imparted by the hydroxy group in the SH2 transition states. In contrast, C–H functionalization of alkanes was largely affected by steric effects.</abstract><cop>Tokyo</cop><pub>The Chemical Society of Japan</pub><doi>10.1246/cl.171068</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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source | Oxford University Press Journals All Titles (1996-Current) |
subjects | Alcohol Aliphatic alcohols Aliphatic compounds Alkanes Hydrogen bonds Selectivity Steric effects |
title | Site-selectivity in TBADT-photocatalyzed C(sp3)–H Functionalization of Saturated Alcohols and Alkanes |
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