Halogenation of aromatic hydrocarbons by halide anion oxidation with poly(heptazine imide) photocatalyst
[Display omitted] •K-PHI photooxidizes halide anions (Cl―, Br―) in aqueous media with oxygen as an acceptor of electrons.•Chlorination as well as bromination of electron rich aromatic hydrocarbons is carried out by K-PHI photocatalyst.•Halogenation of aromatic hydrocarbons proceeds via in situ forma...
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| Veröffentlicht in: | Applied catalysis. B, Environmental Environmental, 2019-07, Vol.248, p.211-217 |
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| container_title | Applied catalysis. B, Environmental |
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| creator | Markushyna, Yevheniia Teutloff, Christian Kurpil, Bogdan Cruz, Daniel Lauermann, Iver Zhao, Yubao Antonietti, Markus Savateev, Aleksandr |
| description | [Display omitted]
•K-PHI photooxidizes halide anions (Cl―, Br―) in aqueous media with oxygen as an acceptor of electrons.•Chlorination as well as bromination of electron rich aromatic hydrocarbons is carried out by K-PHI photocatalyst.•Halogenation of aromatic hydrocarbons proceeds via in situ formation of “HOHal” species by two different pathways.•Solution of NaCl (seawater mimic) is a suitable reagent for photochlorination.
Halocarbons have tremendous significance for the chemical industry. Arylchlorides and arylbromides are typically prepared via Friedel-Crafts reaction, using oxidative halogenation or employing halogen transfer agents, such as N-chloro- and N-bromosuccineimide. Herein, we show that K-PHI, a photocatalyst of the carbon nitride family, can easily photooxidize halide anions (Cl−, Br−) in aqueous media to promote oxidative halogenation of electron rich aromatic compounds. The technique is convenient, safe and gives the haloaromatic products with excellent yields from non-harmful starting reagents in the most sustainable fashion. We show that a solution of NaCl, mimicking seawater, can be used as a reagent for photochlorination. |
| doi_str_mv | 10.1016/j.apcatb.2019.02.016 |
| format | Article |
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•K-PHI photooxidizes halide anions (Cl―, Br―) in aqueous media with oxygen as an acceptor of electrons.•Chlorination as well as bromination of electron rich aromatic hydrocarbons is carried out by K-PHI photocatalyst.•Halogenation of aromatic hydrocarbons proceeds via in situ formation of “HOHal” species by two different pathways.•Solution of NaCl (seawater mimic) is a suitable reagent for photochlorination.
Halocarbons have tremendous significance for the chemical industry. Arylchlorides and arylbromides are typically prepared via Friedel-Crafts reaction, using oxidative halogenation or employing halogen transfer agents, such as N-chloro- and N-bromosuccineimide. Herein, we show that K-PHI, a photocatalyst of the carbon nitride family, can easily photooxidize halide anions (Cl−, Br−) in aqueous media to promote oxidative halogenation of electron rich aromatic compounds. The technique is convenient, safe and gives the haloaromatic products with excellent yields from non-harmful starting reagents in the most sustainable fashion. We show that a solution of NaCl, mimicking seawater, can be used as a reagent for photochlorination.</description><identifier>ISSN: 0926-3373</identifier><identifier>EISSN: 1873-3883</identifier><identifier>DOI: 10.1016/j.apcatb.2019.02.016</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Anions ; Aqueous solutions ; Aromatic compounds ; Aromatic hydrocarbons ; Carbon nitride ; Chemical industry ; Chlorination ; Friedel-Crafts reaction ; Halocarbons ; Halogenation ; Mimicry ; Organic chemistry ; Organic photoredox catalysis ; Organic synthesis ; Oxidation ; Photocatalysts ; Photooxidation ; Reagents ; Seawater ; Sodium chloride ; Sustainable fashion</subject><ispartof>Applied catalysis. B, Environmental, 2019-07, Vol.248, p.211-217</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright Elsevier BV Jul 5, 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c380t-ad36d5a76b6c35ca3f54178f73e2767a1377b6521bd8cc25d3a36b20ea48fc903</citedby><cites>FETCH-LOGICAL-c380t-ad36d5a76b6c35ca3f54178f73e2767a1377b6521bd8cc25d3a36b20ea48fc903</cites><orcidid>0000-0002-5760-6033</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.apcatb.2019.02.016$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Markushyna, Yevheniia</creatorcontrib><creatorcontrib>Teutloff, Christian</creatorcontrib><creatorcontrib>Kurpil, Bogdan</creatorcontrib><creatorcontrib>Cruz, Daniel</creatorcontrib><creatorcontrib>Lauermann, Iver</creatorcontrib><creatorcontrib>Zhao, Yubao</creatorcontrib><creatorcontrib>Antonietti, Markus</creatorcontrib><creatorcontrib>Savateev, Aleksandr</creatorcontrib><title>Halogenation of aromatic hydrocarbons by halide anion oxidation with poly(heptazine imide) photocatalyst</title><title>Applied catalysis. B, Environmental</title><description>[Display omitted]
•K-PHI photooxidizes halide anions (Cl―, Br―) in aqueous media with oxygen as an acceptor of electrons.•Chlorination as well as bromination of electron rich aromatic hydrocarbons is carried out by K-PHI photocatalyst.•Halogenation of aromatic hydrocarbons proceeds via in situ formation of “HOHal” species by two different pathways.•Solution of NaCl (seawater mimic) is a suitable reagent for photochlorination.
Halocarbons have tremendous significance for the chemical industry. Arylchlorides and arylbromides are typically prepared via Friedel-Crafts reaction, using oxidative halogenation or employing halogen transfer agents, such as N-chloro- and N-bromosuccineimide. Herein, we show that K-PHI, a photocatalyst of the carbon nitride family, can easily photooxidize halide anions (Cl−, Br−) in aqueous media to promote oxidative halogenation of electron rich aromatic compounds. The technique is convenient, safe and gives the haloaromatic products with excellent yields from non-harmful starting reagents in the most sustainable fashion. We show that a solution of NaCl, mimicking seawater, can be used as a reagent for photochlorination.</description><subject>Anions</subject><subject>Aqueous solutions</subject><subject>Aromatic compounds</subject><subject>Aromatic hydrocarbons</subject><subject>Carbon nitride</subject><subject>Chemical industry</subject><subject>Chlorination</subject><subject>Friedel-Crafts reaction</subject><subject>Halocarbons</subject><subject>Halogenation</subject><subject>Mimicry</subject><subject>Organic chemistry</subject><subject>Organic photoredox catalysis</subject><subject>Organic synthesis</subject><subject>Oxidation</subject><subject>Photocatalysts</subject><subject>Photooxidation</subject><subject>Reagents</subject><subject>Seawater</subject><subject>Sodium chloride</subject><subject>Sustainable fashion</subject><issn>0926-3373</issn><issn>1873-3883</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kEFP3DAQha2qSF2g_6AHS1zaQ4LtSWLvpRJCUJCQemnP1sR2Gq-ycbANbfrrMQ3nnkbz9L03mkfIJ85qznh3eahxMZj7WjC-r5moi_iO7LiSUIFS8J7s2F50FYCED-Q0pQNjTIBQOzLe4RR-uRmzDzMNA8UYjmUxdFxtDAZjH-ZE-5WOOHnrKM7_wD_ebpbfPo90CdP6eXRLxr9-dtQfC_mFLmPIJSHjtKZ8Tk4GnJL7-DbPyM_bmx_Xd9XD92_311cPlQHFcoUWOtui7PrOQGsQhrbhUg0SnJCdRA5S9l0reG-VMaK1gND1gjls1GD2DM7IxZa7xPD45FLWh_AU53JSC8HkvoFGqkI1G2ViSCm6QS_RHzGumjP92qk-6K1T_dqpZkIXsdi-bjZXPnj2LupkvJuNsz46k7UN_v8BL8nBg1A</recordid><startdate>20190705</startdate><enddate>20190705</enddate><creator>Markushyna, Yevheniia</creator><creator>Teutloff, Christian</creator><creator>Kurpil, Bogdan</creator><creator>Cruz, Daniel</creator><creator>Lauermann, Iver</creator><creator>Zhao, Yubao</creator><creator>Antonietti, Markus</creator><creator>Savateev, Aleksandr</creator><general>Elsevier B.V</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>JG9</scope><scope>KR7</scope><scope>L7M</scope><scope>SOI</scope><orcidid>https://orcid.org/0000-0002-5760-6033</orcidid></search><sort><creationdate>20190705</creationdate><title>Halogenation of aromatic hydrocarbons by halide anion oxidation with poly(heptazine imide) photocatalyst</title><author>Markushyna, Yevheniia ; Teutloff, Christian ; Kurpil, Bogdan ; Cruz, Daniel ; Lauermann, Iver ; Zhao, Yubao ; Antonietti, Markus ; Savateev, Aleksandr</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c380t-ad36d5a76b6c35ca3f54178f73e2767a1377b6521bd8cc25d3a36b20ea48fc903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Anions</topic><topic>Aqueous solutions</topic><topic>Aromatic compounds</topic><topic>Aromatic hydrocarbons</topic><topic>Carbon nitride</topic><topic>Chemical industry</topic><topic>Chlorination</topic><topic>Friedel-Crafts reaction</topic><topic>Halocarbons</topic><topic>Halogenation</topic><topic>Mimicry</topic><topic>Organic chemistry</topic><topic>Organic photoredox catalysis</topic><topic>Organic synthesis</topic><topic>Oxidation</topic><topic>Photocatalysts</topic><topic>Photooxidation</topic><topic>Reagents</topic><topic>Seawater</topic><topic>Sodium chloride</topic><topic>Sustainable fashion</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Markushyna, Yevheniia</creatorcontrib><creatorcontrib>Teutloff, Christian</creatorcontrib><creatorcontrib>Kurpil, Bogdan</creatorcontrib><creatorcontrib>Cruz, Daniel</creatorcontrib><creatorcontrib>Lauermann, Iver</creatorcontrib><creatorcontrib>Zhao, Yubao</creatorcontrib><creatorcontrib>Antonietti, Markus</creatorcontrib><creatorcontrib>Savateev, Aleksandr</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Environment Abstracts</collection><jtitle>Applied catalysis. B, Environmental</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Markushyna, Yevheniia</au><au>Teutloff, Christian</au><au>Kurpil, Bogdan</au><au>Cruz, Daniel</au><au>Lauermann, Iver</au><au>Zhao, Yubao</au><au>Antonietti, Markus</au><au>Savateev, Aleksandr</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Halogenation of aromatic hydrocarbons by halide anion oxidation with poly(heptazine imide) photocatalyst</atitle><jtitle>Applied catalysis. B, Environmental</jtitle><date>2019-07-05</date><risdate>2019</risdate><volume>248</volume><spage>211</spage><epage>217</epage><pages>211-217</pages><issn>0926-3373</issn><eissn>1873-3883</eissn><abstract>[Display omitted]
•K-PHI photooxidizes halide anions (Cl―, Br―) in aqueous media with oxygen as an acceptor of electrons.•Chlorination as well as bromination of electron rich aromatic hydrocarbons is carried out by K-PHI photocatalyst.•Halogenation of aromatic hydrocarbons proceeds via in situ formation of “HOHal” species by two different pathways.•Solution of NaCl (seawater mimic) is a suitable reagent for photochlorination.
Halocarbons have tremendous significance for the chemical industry. Arylchlorides and arylbromides are typically prepared via Friedel-Crafts reaction, using oxidative halogenation or employing halogen transfer agents, such as N-chloro- and N-bromosuccineimide. Herein, we show that K-PHI, a photocatalyst of the carbon nitride family, can easily photooxidize halide anions (Cl−, Br−) in aqueous media to promote oxidative halogenation of electron rich aromatic compounds. The technique is convenient, safe and gives the haloaromatic products with excellent yields from non-harmful starting reagents in the most sustainable fashion. We show that a solution of NaCl, mimicking seawater, can be used as a reagent for photochlorination.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.apcatb.2019.02.016</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-5760-6033</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Anions Aqueous solutions Aromatic compounds Aromatic hydrocarbons Carbon nitride Chemical industry Chlorination Friedel-Crafts reaction Halocarbons Halogenation Mimicry Organic chemistry Organic photoredox catalysis Organic synthesis Oxidation Photocatalysts Photooxidation Reagents Seawater Sodium chloride Sustainable fashion |
| title | Halogenation of aromatic hydrocarbons by halide anion oxidation with poly(heptazine imide) photocatalyst |
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