Dinuclear gold(I)‐N‐heterocyclic carbene complexes: Synthesis, characterization, and catalytic application for hydrohydrazidation of terminal alkynes
Dinuclear gold(I)‐N‐heterocyclic carbene complexes were developed for the hydrohydrazidation of terminal alkynes. The gold(I)‐N‐heterocyclic carbene complexes 2a‐2b were synthesized in good yields from silver complexes synthesized in situ, which in turn were obtained from the corresponding imidazoli...
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| Veröffentlicht in: | Applied organometallic chemistry 2020-11, Vol.34 (11), p.n/a |
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| creator | Yadav, Seema Ray, Sriparna Singh, Ajeet Mobin, Shaikh M. Roy, Tapta Kanchan Dash, Chandrakanta |
| description | Dinuclear gold(I)‐N‐heterocyclic carbene complexes were developed for the hydrohydrazidation of terminal alkynes. The gold(I)‐N‐heterocyclic carbene complexes 2a‐2b were synthesized in good yields from silver complexes synthesized in situ, which in turn were obtained from the corresponding imidazolium salts with Ag2O in dichloromethane as a solvent. The new air‐stable gold(I)‐NHC complexes, 2a‐2b, were characterized using NMR spectroscopy, elemental analysis, infrared, and mass spectroscopy studies. The gold(I) complex 2a was characterized using X‐ray crystallography. Bis‐N‐heterocyclic carbene–based gold(I) complexes 2a‐2b exhibited excellent catalytic activities for hydrohydrazidation of terminal alkynes yielding acylhydrazone derivatives. The working catalytic system can be used in gram‐scale synthesis. In addition, the catalytic reaction mechanism of the hydrohydrazidation of terminal alkynes by gold(I)‐NHC complex was studied in detail using density functional theory.
Air‐ and moisture‐stable dinuclear gold‐N‐heterocyclic carbene complexes were synthesized and characterized. The dinuclear gold(I)‐NHC complexes were successfully used as a catalyst for the hydrohydrazidation of terminal alkynes. The catalytic reaction mechanism was investigated using density functional theory. |
| doi_str_mv | 10.1002/aoc.5942 |
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Air‐ and moisture‐stable dinuclear gold‐N‐heterocyclic carbene complexes were synthesized and characterized. The dinuclear gold(I)‐NHC complexes were successfully used as a catalyst for the hydrohydrazidation of terminal alkynes. The catalytic reaction mechanism was investigated using density functional theory.</description><identifier>ISSN: 0268-2605</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.5942</identifier><language>eng</language><publisher>Chichester: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Chemical analysis ; Chemical synthesis ; Chemistry ; Crystallography ; Density functional theory ; DFT study ; Dichloromethane ; Gold ; hydrohydrazidation ; Infrared analysis ; mechanism ; NMR spectroscopy ; N‐heterocyclic carbene ; Reaction mechanisms ; Silver compounds ; Spectrum analysis</subject><ispartof>Applied organometallic chemistry, 2020-11, Vol.34 (11), p.n/a</ispartof><rights>2020 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3302-3f4aad507197d3f3ec7eecc05b132c4404f618a4352ca451348f9102e283e2153</citedby><cites>FETCH-LOGICAL-c3302-3f4aad507197d3f3ec7eecc05b132c4404f618a4352ca451348f9102e283e2153</cites><orcidid>0000-0002-2665-5123 ; 0000-0002-6945-1366</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%2Faoc.5942$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.5942$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Yadav, Seema</creatorcontrib><creatorcontrib>Ray, Sriparna</creatorcontrib><creatorcontrib>Singh, Ajeet</creatorcontrib><creatorcontrib>Mobin, Shaikh M.</creatorcontrib><creatorcontrib>Roy, Tapta Kanchan</creatorcontrib><creatorcontrib>Dash, Chandrakanta</creatorcontrib><title>Dinuclear gold(I)‐N‐heterocyclic carbene complexes: Synthesis, characterization, and catalytic application for hydrohydrazidation of terminal alkynes</title><title>Applied organometallic chemistry</title><description>Dinuclear gold(I)‐N‐heterocyclic carbene complexes were developed for the hydrohydrazidation of terminal alkynes. The gold(I)‐N‐heterocyclic carbene complexes 2a‐2b were synthesized in good yields from silver complexes synthesized in situ, which in turn were obtained from the corresponding imidazolium salts with Ag2O in dichloromethane as a solvent. The new air‐stable gold(I)‐NHC complexes, 2a‐2b, were characterized using NMR spectroscopy, elemental analysis, infrared, and mass spectroscopy studies. The gold(I) complex 2a was characterized using X‐ray crystallography. Bis‐N‐heterocyclic carbene–based gold(I) complexes 2a‐2b exhibited excellent catalytic activities for hydrohydrazidation of terminal alkynes yielding acylhydrazone derivatives. The working catalytic system can be used in gram‐scale synthesis. In addition, the catalytic reaction mechanism of the hydrohydrazidation of terminal alkynes by gold(I)‐NHC complex was studied in detail using density functional theory.
Air‐ and moisture‐stable dinuclear gold‐N‐heterocyclic carbene complexes were synthesized and characterized. The dinuclear gold(I)‐NHC complexes were successfully used as a catalyst for the hydrohydrazidation of terminal alkynes. The catalytic reaction mechanism was investigated using density functional theory.</description><subject>Alkynes</subject><subject>Chemical analysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Crystallography</subject><subject>Density functional theory</subject><subject>DFT study</subject><subject>Dichloromethane</subject><subject>Gold</subject><subject>hydrohydrazidation</subject><subject>Infrared analysis</subject><subject>mechanism</subject><subject>NMR spectroscopy</subject><subject>N‐heterocyclic carbene</subject><subject>Reaction mechanisms</subject><subject>Silver compounds</subject><subject>Spectrum analysis</subject><issn>0268-2605</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kM9O3DAQxi1EJRaKxCNY6oVKGzr-k82aG1oKRULlQDlHgzNhTb1xsLOCcOoj9Mrr9UnqZXvtYWakmd_3afQxdiTgRADILxjsSWm03GETAcYUUCmzyyYgZ_NCzqDcY_spPQKAmQk9YW_nrltbTxj5Q_DN8dXnP79-f8-1pIFisKP1znKL8Z464jasek8vlE757dgNS0ouTbldYkSbcfeKgwvdlGPXZM2AfhyyGvs-m7yfeBsiX45NDJuGr67ZrkPLs37lOvQc_c-xo_SRfWjRJzr8Nw_Y3cXXH4tvxfXN5dXi7LqwSoEsVKsRmxIqYapGtYpsRWQtlPdCSas16HYm5qhVKS3qUig9b40ASXKuSIpSHbBPW98-hqc1paF-DOuYH0m11NpoqEwpM3W8pWwMKUVq6z66FcaxFlBvgq9z8PUm-IwWW_TZeRr_y9VnN4t3_i9vqojl</recordid><startdate>202011</startdate><enddate>202011</enddate><creator>Yadav, Seema</creator><creator>Ray, Sriparna</creator><creator>Singh, Ajeet</creator><creator>Mobin, Shaikh M.</creator><creator>Roy, Tapta Kanchan</creator><creator>Dash, Chandrakanta</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-2665-5123</orcidid><orcidid>https://orcid.org/0000-0002-6945-1366</orcidid></search><sort><creationdate>202011</creationdate><title>Dinuclear gold(I)‐N‐heterocyclic carbene complexes: Synthesis, characterization, and catalytic application for hydrohydrazidation of terminal alkynes</title><author>Yadav, Seema ; Ray, Sriparna ; Singh, Ajeet ; Mobin, Shaikh M. ; Roy, Tapta Kanchan ; Dash, Chandrakanta</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3302-3f4aad507197d3f3ec7eecc05b132c4404f618a4352ca451348f9102e283e2153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkynes</topic><topic>Chemical analysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Crystallography</topic><topic>Density functional theory</topic><topic>DFT study</topic><topic>Dichloromethane</topic><topic>Gold</topic><topic>hydrohydrazidation</topic><topic>Infrared analysis</topic><topic>mechanism</topic><topic>NMR spectroscopy</topic><topic>N‐heterocyclic carbene</topic><topic>Reaction mechanisms</topic><topic>Silver compounds</topic><topic>Spectrum analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yadav, Seema</creatorcontrib><creatorcontrib>Ray, Sriparna</creatorcontrib><creatorcontrib>Singh, Ajeet</creatorcontrib><creatorcontrib>Mobin, Shaikh M.</creatorcontrib><creatorcontrib>Roy, Tapta Kanchan</creatorcontrib><creatorcontrib>Dash, Chandrakanta</creatorcontrib><collection>CrossRef</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 organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yadav, Seema</au><au>Ray, Sriparna</au><au>Singh, Ajeet</au><au>Mobin, Shaikh M.</au><au>Roy, Tapta Kanchan</au><au>Dash, Chandrakanta</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dinuclear gold(I)‐N‐heterocyclic carbene complexes: Synthesis, characterization, and catalytic application for hydrohydrazidation of terminal alkynes</atitle><jtitle>Applied organometallic chemistry</jtitle><date>2020-11</date><risdate>2020</risdate><volume>34</volume><issue>11</issue><epage>n/a</epage><issn>0268-2605</issn><eissn>1099-0739</eissn><abstract>Dinuclear gold(I)‐N‐heterocyclic carbene complexes were developed for the hydrohydrazidation of terminal alkynes. The gold(I)‐N‐heterocyclic carbene complexes 2a‐2b were synthesized in good yields from silver complexes synthesized in situ, which in turn were obtained from the corresponding imidazolium salts with Ag2O in dichloromethane as a solvent. The new air‐stable gold(I)‐NHC complexes, 2a‐2b, were characterized using NMR spectroscopy, elemental analysis, infrared, and mass spectroscopy studies. The gold(I) complex 2a was characterized using X‐ray crystallography. Bis‐N‐heterocyclic carbene–based gold(I) complexes 2a‐2b exhibited excellent catalytic activities for hydrohydrazidation of terminal alkynes yielding acylhydrazone derivatives. The working catalytic system can be used in gram‐scale synthesis. In addition, the catalytic reaction mechanism of the hydrohydrazidation of terminal alkynes by gold(I)‐NHC complex was studied in detail using density functional theory.
Air‐ and moisture‐stable dinuclear gold‐N‐heterocyclic carbene complexes were synthesized and characterized. The dinuclear gold(I)‐NHC complexes were successfully used as a catalyst for the hydrohydrazidation of terminal alkynes. The catalytic reaction mechanism was investigated using density functional theory.</abstract><cop>Chichester</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/aoc.5942</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-2665-5123</orcidid><orcidid>https://orcid.org/0000-0002-6945-1366</orcidid></addata></record> |
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| subjects | Alkynes Chemical analysis Chemical synthesis Chemistry Crystallography Density functional theory DFT study Dichloromethane Gold hydrohydrazidation Infrared analysis mechanism NMR spectroscopy N‐heterocyclic carbene Reaction mechanisms Silver compounds Spectrum analysis |
| title | Dinuclear gold(I)‐N‐heterocyclic carbene complexes: Synthesis, characterization, and catalytic application for hydrohydrazidation of terminal alkynes |
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