Improved Synthesis of 1,2,3‐Triazolium Salts via Oxidative [3+2] Cycloaddition of Triazenes with Alkynes and Their Deprotonative Functionalization
1,2,3‐Triazolium units are present in various functionalized molecules, including mesoionic carbenes, organocatalysts, and anion recognition receptors. While the oxidative [3+2] cycloaddition of triazenes with alkynes is one of the most efficient methods to construct the 1,2,3‐triazolium skeleton, t...
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| Veröffentlicht in: | Asian journal of organic chemistry 2021-04, Vol.10 (4), p.901-905 |
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| creator | Sawaguchi, Daiki Hayakawa, Shunsuke Sakuma, Masaaki Niitsuma, Kenta Kase, Daiya Michii, Shota Ozawa, Miyuki Sakai, Yusuke Sakamaki, Kentaro Ueyama, Kyohei Haraguchi, Ryosuke |
| description | 1,2,3‐Triazolium units are present in various functionalized molecules, including mesoionic carbenes, organocatalysts, and anion recognition receptors. While the oxidative [3+2] cycloaddition of triazenes with alkynes is one of the most efficient methods to construct the 1,2,3‐triazolium skeleton, the effect of reaction parameters and substrate scope in the reaction has not been fully studied. Herein, we developed a practical protocol for the synthesis of 1,2,3‐triazolium salts and significantly expanded the substrate scope of triazenes and alkynes. Also, an efficient method for the deprotonative functionalization of 1,2,3‐triazolium salts was achieved.
A structurally diverse 1,2,3‐triazolium salts were successfully synthesized through oxidative [3+2] cycloaddition of triazenes and alkynes. Moreover, a practical method for the deprotonative functionalization of 1,2,3‐triazolium salts under air was also developed. |
| doi_str_mv | 10.1002/ajoc.202100033 |
| format | Article |
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A structurally diverse 1,2,3‐triazolium salts were successfully synthesized through oxidative [3+2] cycloaddition of triazenes and alkynes. Moreover, a practical method for the deprotonative functionalization of 1,2,3‐triazolium salts under air was also developed.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202100033</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>1,2,3-triazolium salt ; [3+2] cycloaddition ; Alkynes ; Carbenes ; cationic phosphine ; Cycloaddition ; halogen bonding ; Organic chemistry ; Substrates ; Synthesis ; triazene</subject><ispartof>Asian journal of organic chemistry, 2021-04, Vol.10 (4), p.901-905</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3173-f84930e961768d715fbb9d3b9749cf03a1e23c2ea134ab8edbb731264094dfb73</citedby><cites>FETCH-LOGICAL-c3173-f84930e961768d715fbb9d3b9749cf03a1e23c2ea134ab8edbb731264094dfb73</cites><orcidid>0000-0001-6703-8036</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%2Fajoc.202100033$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202100033$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27911,27912,45561,45562</link.rule.ids></links><search><creatorcontrib>Sawaguchi, Daiki</creatorcontrib><creatorcontrib>Hayakawa, Shunsuke</creatorcontrib><creatorcontrib>Sakuma, Masaaki</creatorcontrib><creatorcontrib>Niitsuma, Kenta</creatorcontrib><creatorcontrib>Kase, Daiya</creatorcontrib><creatorcontrib>Michii, Shota</creatorcontrib><creatorcontrib>Ozawa, Miyuki</creatorcontrib><creatorcontrib>Sakai, Yusuke</creatorcontrib><creatorcontrib>Sakamaki, Kentaro</creatorcontrib><creatorcontrib>Ueyama, Kyohei</creatorcontrib><creatorcontrib>Haraguchi, Ryosuke</creatorcontrib><title>Improved Synthesis of 1,2,3‐Triazolium Salts via Oxidative [3+2] Cycloaddition of Triazenes with Alkynes and Their Deprotonative Functionalization</title><title>Asian journal of organic chemistry</title><description>1,2,3‐Triazolium units are present in various functionalized molecules, including mesoionic carbenes, organocatalysts, and anion recognition receptors. While the oxidative [3+2] cycloaddition of triazenes with alkynes is one of the most efficient methods to construct the 1,2,3‐triazolium skeleton, the effect of reaction parameters and substrate scope in the reaction has not been fully studied. Herein, we developed a practical protocol for the synthesis of 1,2,3‐triazolium salts and significantly expanded the substrate scope of triazenes and alkynes. Also, an efficient method for the deprotonative functionalization of 1,2,3‐triazolium salts was achieved.
A structurally diverse 1,2,3‐triazolium salts were successfully synthesized through oxidative [3+2] cycloaddition of triazenes and alkynes. Moreover, a practical method for the deprotonative functionalization of 1,2,3‐triazolium salts under air was also developed.</description><subject>1,2,3-triazolium salt</subject><subject>[3+2] cycloaddition</subject><subject>Alkynes</subject><subject>Carbenes</subject><subject>cationic phosphine</subject><subject>Cycloaddition</subject><subject>halogen bonding</subject><subject>Organic chemistry</subject><subject>Substrates</subject><subject>Synthesis</subject><subject>triazene</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhS0EEhV0ZbbESFP8k8TxWAUKRZU6tEwIRU7sqC5pXOKkJZ14BAaekCchIaiMTPdc6Xz3Hh0ALjAaYoTItViZZEgQaRZE6RHoEcyp4wXYOz5oxE5B39pVY0GMcUx4D3xO1pvCbJWE8zovl8pqC00K8YAM6Nf7x6LQYm8yXa3hXGSlhVst4OxNS1HqrYJP9Io8w7BOMiOk1KU2eUv_UCpXFu50uYSj7KVuF5FLuFgqXcAb1TwtTd5dGVd50qIi03vRinNwkorMqv7vPAOP49tFeO9MZ3eTcDR1EooZddLA5RQp7mPmB5JhL41jLmnMmcuTFFGBFaEJUQJTV8SBknHMKCa-i7gr00afgcvubpPmtVK2jFamKpocNiIedin1KQka17BzJYWxtlBptCn0WhR1hFHUlh-15UeH8huAd8BOZ6r-xx2NHmbhH_sN9ZyKwg</recordid><startdate>202104</startdate><enddate>202104</enddate><creator>Sawaguchi, Daiki</creator><creator>Hayakawa, Shunsuke</creator><creator>Sakuma, Masaaki</creator><creator>Niitsuma, Kenta</creator><creator>Kase, Daiya</creator><creator>Michii, Shota</creator><creator>Ozawa, Miyuki</creator><creator>Sakai, Yusuke</creator><creator>Sakamaki, Kentaro</creator><creator>Ueyama, Kyohei</creator><creator>Haraguchi, Ryosuke</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-6703-8036</orcidid></search><sort><creationdate>202104</creationdate><title>Improved Synthesis of 1,2,3‐Triazolium Salts via Oxidative [3+2] Cycloaddition of Triazenes with Alkynes and Their Deprotonative Functionalization</title><author>Sawaguchi, Daiki ; Hayakawa, Shunsuke ; Sakuma, Masaaki ; Niitsuma, Kenta ; Kase, Daiya ; Michii, Shota ; Ozawa, Miyuki ; Sakai, Yusuke ; Sakamaki, Kentaro ; Ueyama, Kyohei ; Haraguchi, Ryosuke</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3173-f84930e961768d715fbb9d3b9749cf03a1e23c2ea134ab8edbb731264094dfb73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>1,2,3-triazolium salt</topic><topic>[3+2] cycloaddition</topic><topic>Alkynes</topic><topic>Carbenes</topic><topic>cationic phosphine</topic><topic>Cycloaddition</topic><topic>halogen bonding</topic><topic>Organic chemistry</topic><topic>Substrates</topic><topic>Synthesis</topic><topic>triazene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sawaguchi, Daiki</creatorcontrib><creatorcontrib>Hayakawa, Shunsuke</creatorcontrib><creatorcontrib>Sakuma, Masaaki</creatorcontrib><creatorcontrib>Niitsuma, Kenta</creatorcontrib><creatorcontrib>Kase, Daiya</creatorcontrib><creatorcontrib>Michii, Shota</creatorcontrib><creatorcontrib>Ozawa, Miyuki</creatorcontrib><creatorcontrib>Sakai, Yusuke</creatorcontrib><creatorcontrib>Sakamaki, Kentaro</creatorcontrib><creatorcontrib>Ueyama, Kyohei</creatorcontrib><creatorcontrib>Haraguchi, Ryosuke</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sawaguchi, Daiki</au><au>Hayakawa, Shunsuke</au><au>Sakuma, Masaaki</au><au>Niitsuma, Kenta</au><au>Kase, Daiya</au><au>Michii, Shota</au><au>Ozawa, Miyuki</au><au>Sakai, Yusuke</au><au>Sakamaki, Kentaro</au><au>Ueyama, Kyohei</au><au>Haraguchi, Ryosuke</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Improved Synthesis of 1,2,3‐Triazolium Salts via Oxidative [3+2] Cycloaddition of Triazenes with Alkynes and Their Deprotonative Functionalization</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2021-04</date><risdate>2021</risdate><volume>10</volume><issue>4</issue><spage>901</spage><epage>905</epage><pages>901-905</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>1,2,3‐Triazolium units are present in various functionalized molecules, including mesoionic carbenes, organocatalysts, and anion recognition receptors. While the oxidative [3+2] cycloaddition of triazenes with alkynes is one of the most efficient methods to construct the 1,2,3‐triazolium skeleton, the effect of reaction parameters and substrate scope in the reaction has not been fully studied. Herein, we developed a practical protocol for the synthesis of 1,2,3‐triazolium salts and significantly expanded the substrate scope of triazenes and alkynes. Also, an efficient method for the deprotonative functionalization of 1,2,3‐triazolium salts was achieved.
A structurally diverse 1,2,3‐triazolium salts were successfully synthesized through oxidative [3+2] cycloaddition of triazenes and alkynes. Moreover, a practical method for the deprotonative functionalization of 1,2,3‐triazolium salts under air was also developed.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202100033</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-6703-8036</orcidid></addata></record> |
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| subjects | 1,2,3-triazolium salt [3+2] cycloaddition Alkynes Carbenes cationic phosphine Cycloaddition halogen bonding Organic chemistry Substrates Synthesis triazene |
| title | Improved Synthesis of 1,2,3‐Triazolium Salts via Oxidative [3+2] Cycloaddition of Triazenes with Alkynes and Their Deprotonative Functionalization |
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