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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry letters 2018-01, Vol.47 (2), p.207-209
Hauptverfasser: Fukuyama, Takahide, Yamada, Keiichi, Nishikawa, Tomohiro, Ravelli, Davide, Fagnoni, Maurizio, Ryu, Illhyong
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 209
container_issue 2
container_start_page 207
container_title Chemistry letters
container_volume 47
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
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2241359886</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2241359886</sourcerecordid><originalsourceid>FETCH-LOGICAL-c504t-adf3d0edd590d43783b1d496c65d130f5db8715b8a1ff8e205bd1550f735f1653</originalsourceid><addsrcrecordid>eNplkL9OwzAQhy0EEqUw8AaRWOiQYsex44ylUIpUiaFljhz_oS5uHGIHKZ14B96QJyFVKzEw3Z303ae7HwDXCI5RktI7YccoQ5CyEzBAOGUxzBA5BQOIKY0zmCTn4ML7DYSQ5TgZgLelCSr2yioRzKcJXWSqaHU_eVjF9doFJ3jgttspGU1vfY1HP1_f82jWVj3tKm7Nju-byOloyUPb8NCTEyvc2lkf8Wo_vPNK-Utwprn16upYh-B19riazuPFy9PzdLKIBYFpiLnUWEIlJcmhTHHGcIlkmlNBiUQYaiJL1j9UMo60ZiqBpJSIEKgzTDSiBA_BzcFbN-6jVT4UG9c2_aW-SJIUYZIzRntqdKBE47xvlC7qxmx50xUIFvscC2GLQ449S4_sWm2N6E1OGBW6Da959Wf_v_gLtu146w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2241359886</pqid></control><display><type>article</type><title>Site-selectivity in TBADT-photocatalyzed C(sp3)–H Functionalization of Saturated Alcohols and Alkanes</title><source>Oxford University Press Journals All Titles (1996-Current)</source><creator>Fukuyama, Takahide ; Yamada, Keiichi ; Nishikawa, Tomohiro ; Ravelli, Davide ; Fagnoni, Maurizio ; Ryu, Illhyong</creator><creatorcontrib>Fukuyama, Takahide ; Yamada, Keiichi ; Nishikawa, Tomohiro ; Ravelli, Davide ; Fagnoni, Maurizio ; Ryu, Illhyong</creatorcontrib><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.</description><identifier>ISSN: 0366-7022</identifier><identifier>EISSN: 1348-0715</identifier><identifier>DOI: 10.1246/cl.171068</identifier><language>eng</language><publisher>Tokyo: The Chemical Society of Japan</publisher><subject>Alcohol ; Aliphatic alcohols ; Aliphatic compounds ; Alkanes ; Hydrogen bonds ; Selectivity ; Steric effects</subject><ispartof>Chemistry letters, 2018-01, Vol.47 (2), p.207-209</ispartof><rights>The Chemical Society of Japan</rights><rights>Copyright Chemical Society of Japan 2018</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c504t-adf3d0edd590d43783b1d496c65d130f5db8715b8a1ff8e205bd1550f735f1653</citedby><cites>FETCH-LOGICAL-c504t-adf3d0edd590d43783b1d496c65d130f5db8715b8a1ff8e205bd1550f735f1653</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></links><search><creatorcontrib>Fukuyama, Takahide</creatorcontrib><creatorcontrib>Yamada, Keiichi</creatorcontrib><creatorcontrib>Nishikawa, Tomohiro</creatorcontrib><creatorcontrib>Ravelli, Davide</creatorcontrib><creatorcontrib>Fagnoni, Maurizio</creatorcontrib><creatorcontrib>Ryu, Illhyong</creatorcontrib><title>Site-selectivity in TBADT-photocatalyzed C(sp3)–H Functionalization of Saturated Alcohols and Alkanes</title><title>Chemistry letters</title><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.</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>
fulltext fulltext
identifier ISSN: 0366-7022
ispartof Chemistry letters, 2018-01, Vol.47 (2), p.207-209
issn 0366-7022
1348-0715
language eng
recordid cdi_proquest_journals_2241359886
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
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T23%3A40%3A50IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Site-selectivity%20in%20TBADT-photocatalyzed%20C(sp3)%E2%80%93H%20Functionalization%20of%20Saturated%20Alcohols%20and%20Alkanes&rft.jtitle=Chemistry%20letters&rft.au=Fukuyama,%20Takahide&rft.date=2018-01-01&rft.volume=47&rft.issue=2&rft.spage=207&rft.epage=209&rft.pages=207-209&rft.issn=0366-7022&rft.eissn=1348-0715&rft_id=info:doi/10.1246/cl.171068&rft_dat=%3Cproquest_cross%3E2241359886%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2241359886&rft_id=info:pmid/&rfr_iscdi=true