Synergistic catalysis of the Brönsted acid and highly dispersed Cu on the mesoporous Beta zeolite in the intermolecular aminoazidation of styrene

[Display omitted] •Cu/Beta-M exhibits high activity in the intermolecular aminoazidation of styrene.•Brönsted acid and Cu+ (Cu2+) species have a synergetic catalysis.•Brönsted acidic sites on zeolite chemisorb the styrene and activate the CC bond.•Cu+ (Cu2+) favor the formation of electrophile from...

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Veröffentlicht in:Applied catalysis. A, General General, 2021-01, Vol.609, p.117907, Article 117907
Hauptverfasser: Fu, Wenqian, Yin, Chengyou, Feng, Yu, Zhang, Lei, Cheng, Feng, Fang, Zhongxue, Zhu, Chaojie, Tang, Tiandi
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container_title Applied catalysis. A, General
container_volume 609
creator Fu, Wenqian
Yin, Chengyou
Feng, Yu
Zhang, Lei
Cheng, Feng
Fang, Zhongxue
Zhu, Chaojie
Tang, Tiandi
description [Display omitted] •Cu/Beta-M exhibits high activity in the intermolecular aminoazidation of styrene.•Brönsted acid and Cu+ (Cu2+) species have a synergetic catalysis.•Brönsted acidic sites on zeolite chemisorb the styrene and activate the CC bond.•Cu+ (Cu2+) favor the formation of electrophile from N-fluorobenzenesulfonimide. Acidic mesoporous Beta zeolite supported Cu (Cu/Beta-M) catalyst shows superior catalytic performance in the difunctionalization of styrenes with N-fluorobenzenesulfonimide (F-N(SO2Ph)2) and azidotrimethylsilane, compared with basic mesoporous ETS-10-M and acid-free Silicalite-1-M support Cu catalysts. The Brönsted acid, copper species and mesoporosity in the Cu/Beta-M catalyst jointly contribute to this reaction. The Cu/Beta-M catalyst can induce the chemisorption of the styrenes through interaction of CC bond with the Brönsted acidic sites, promoting the activation of the CC bond. Meanwhile, the Cu species in Cu/Beta-M can catalyze F-N(SO2Ph)2 to transform into the -N(SO2Ph)2 electrophile, which attacks the activated CC bond of styrenes, leading to the catalyst with high activity and product selectivity. In addition, the styrenes with electron-donating groups have high electron density of the π-conjugated system, which can strengthen the interaction of CC bond with the Brönsted acidic sites, leading to the substrates with high reactivity.
doi_str_mv 10.1016/j.apcata.2020.117907
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Acidic mesoporous Beta zeolite supported Cu (Cu/Beta-M) catalyst shows superior catalytic performance in the difunctionalization of styrenes with N-fluorobenzenesulfonimide (F-N(SO2Ph)2) and azidotrimethylsilane, compared with basic mesoporous ETS-10-M and acid-free Silicalite-1-M support Cu catalysts. The Brönsted acid, copper species and mesoporosity in the Cu/Beta-M catalyst jointly contribute to this reaction. The Cu/Beta-M catalyst can induce the chemisorption of the styrenes through interaction of CC bond with the Brönsted acidic sites, promoting the activation of the CC bond. Meanwhile, the Cu species in Cu/Beta-M can catalyze F-N(SO2Ph)2 to transform into the -N(SO2Ph)2 electrophile, which attacks the activated CC bond of styrenes, leading to the catalyst with high activity and product selectivity. In addition, the styrenes with electron-donating groups have high electron density of the π-conjugated system, which can strengthen the interaction of CC bond with the Brönsted acidic sites, leading to the substrates with high reactivity.</description><identifier>ISSN: 0926-860X</identifier><identifier>EISSN: 1873-3875</identifier><identifier>DOI: 10.1016/j.apcata.2020.117907</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Brönsted acid ; Catalysis ; Catalysts ; Chemisorption ; Copper ; Cu catalyst ; Electron density ; Mesoporous Beta zeolite ; Selectivity ; Silicalite ; Styrene difunctionalization ; Styrenes ; Substrates ; Zeolites</subject><ispartof>Applied catalysis. 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A, General</title><description>[Display omitted] •Cu/Beta-M exhibits high activity in the intermolecular aminoazidation of styrene.•Brönsted acid and Cu+ (Cu2+) species have a synergetic catalysis.•Brönsted acidic sites on zeolite chemisorb the styrene and activate the CC bond.•Cu+ (Cu2+) favor the formation of electrophile from N-fluorobenzenesulfonimide. Acidic mesoporous Beta zeolite supported Cu (Cu/Beta-M) catalyst shows superior catalytic performance in the difunctionalization of styrenes with N-fluorobenzenesulfonimide (F-N(SO2Ph)2) and azidotrimethylsilane, compared with basic mesoporous ETS-10-M and acid-free Silicalite-1-M support Cu catalysts. The Brönsted acid, copper species and mesoporosity in the Cu/Beta-M catalyst jointly contribute to this reaction. The Cu/Beta-M catalyst can induce the chemisorption of the styrenes through interaction of CC bond with the Brönsted acidic sites, promoting the activation of the CC bond. Meanwhile, the Cu species in Cu/Beta-M can catalyze F-N(SO2Ph)2 to transform into the -N(SO2Ph)2 electrophile, which attacks the activated CC bond of styrenes, leading to the catalyst with high activity and product selectivity. In addition, the styrenes with electron-donating groups have high electron density of the π-conjugated system, which can strengthen the interaction of CC bond with the Brönsted acidic sites, leading to the substrates with high reactivity.</description><subject>Brönsted acid</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemisorption</subject><subject>Copper</subject><subject>Cu catalyst</subject><subject>Electron density</subject><subject>Mesoporous Beta zeolite</subject><subject>Selectivity</subject><subject>Silicalite</subject><subject>Styrene difunctionalization</subject><subject>Styrenes</subject><subject>Substrates</subject><subject>Zeolites</subject><issn>0926-860X</issn><issn>1873-3875</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9UMFq3DAUFKGFbNP8QQ6Cnr2RZNmyL4FmadJAoIckkJvQSk9ZLV7JleSC8xn9mP5AfqzauOde3oM382aYQeiCkjUltL3cr9WoVVZrRlg5UdETcYJWtBN1VXei-YBWpGdt1bXk-RR9SmlPCGG8b1bo98PsIb64lJ3GR41hTi7hYHHeAb6Ob398ymCw0q4Mb_DOveyGGRuXRoipIJsJB__OPkAKY4hhSvgassKvEAaXAbsFdj5DPIQB9DSoiNXB-aBenVHZFYHimPIcwcNn9NGqIcH5v32Gnm6-PW6-V_c_bu82X-8rXdc8VxpaVltbkmy3QIXoLSMKhOnUlghSc93xxraCWmZ7y6lo2oYLVQtuTau2htVn6MuiO8bwc4KU5T5M0RdLybjoOkYa1hYWX1g6hpQiWDlGd1BxlpTIY_tyL5f25bF9ubRf3q6WNygJfjmIMmkHXoNxEXSWJrj_C_wFzrSTTA</recordid><startdate>20210105</startdate><enddate>20210105</enddate><creator>Fu, Wenqian</creator><creator>Yin, Chengyou</creator><creator>Feng, Yu</creator><creator>Zhang, Lei</creator><creator>Cheng, Feng</creator><creator>Fang, Zhongxue</creator><creator>Zhu, Chaojie</creator><creator>Tang, Tiandi</creator><general>Elsevier B.V</general><general>Elsevier Science SA</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-1172-3672</orcidid></search><sort><creationdate>20210105</creationdate><title>Synergistic catalysis of the Brönsted acid and highly dispersed Cu on the mesoporous Beta zeolite in the intermolecular aminoazidation of styrene</title><author>Fu, Wenqian ; Yin, Chengyou ; Feng, Yu ; Zhang, Lei ; Cheng, Feng ; Fang, Zhongxue ; Zhu, Chaojie ; Tang, Tiandi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c334t-ce623ff000bbe1779f20ae7d8ab07034c845f671f2f9f41756547a374fd6abd23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Brönsted acid</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemisorption</topic><topic>Copper</topic><topic>Cu catalyst</topic><topic>Electron density</topic><topic>Mesoporous Beta zeolite</topic><topic>Selectivity</topic><topic>Silicalite</topic><topic>Styrene difunctionalization</topic><topic>Styrenes</topic><topic>Substrates</topic><topic>Zeolites</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fu, Wenqian</creatorcontrib><creatorcontrib>Yin, Chengyou</creatorcontrib><creatorcontrib>Feng, Yu</creatorcontrib><creatorcontrib>Zhang, Lei</creatorcontrib><creatorcontrib>Cheng, Feng</creatorcontrib><creatorcontrib>Fang, Zhongxue</creatorcontrib><creatorcontrib>Zhu, Chaojie</creatorcontrib><creatorcontrib>Tang, Tiandi</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Applied catalysis. 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A, General</jtitle><date>2021-01-05</date><risdate>2021</risdate><volume>609</volume><spage>117907</spage><pages>117907-</pages><artnum>117907</artnum><issn>0926-860X</issn><eissn>1873-3875</eissn><abstract>[Display omitted] •Cu/Beta-M exhibits high activity in the intermolecular aminoazidation of styrene.•Brönsted acid and Cu+ (Cu2+) species have a synergetic catalysis.•Brönsted acidic sites on zeolite chemisorb the styrene and activate the CC bond.•Cu+ (Cu2+) favor the formation of electrophile from N-fluorobenzenesulfonimide. Acidic mesoporous Beta zeolite supported Cu (Cu/Beta-M) catalyst shows superior catalytic performance in the difunctionalization of styrenes with N-fluorobenzenesulfonimide (F-N(SO2Ph)2) and azidotrimethylsilane, compared with basic mesoporous ETS-10-M and acid-free Silicalite-1-M support Cu catalysts. The Brönsted acid, copper species and mesoporosity in the Cu/Beta-M catalyst jointly contribute to this reaction. The Cu/Beta-M catalyst can induce the chemisorption of the styrenes through interaction of CC bond with the Brönsted acidic sites, promoting the activation of the CC bond. Meanwhile, the Cu species in Cu/Beta-M can catalyze F-N(SO2Ph)2 to transform into the -N(SO2Ph)2 electrophile, which attacks the activated CC bond of styrenes, leading to the catalyst with high activity and product selectivity. In addition, the styrenes with electron-donating groups have high electron density of the π-conjugated system, which can strengthen the interaction of CC bond with the Brönsted acidic sites, leading to the substrates with high reactivity.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.apcata.2020.117907</doi><orcidid>https://orcid.org/0000-0002-1172-3672</orcidid></addata></record>
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subjects Brönsted acid
Catalysis
Catalysts
Chemisorption
Copper
Cu catalyst
Electron density
Mesoporous Beta zeolite
Selectivity
Silicalite
Styrene difunctionalization
Styrenes
Substrates
Zeolites
title Synergistic catalysis of the Brönsted acid and highly dispersed Cu on the mesoporous Beta zeolite in the intermolecular aminoazidation of styrene
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