A CO 2 -mediated base catalysis approach for the hydration of triple bonds in ionic liquids
Herein, we report a CO 2 -mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO 2 ( e.g. , azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the an...
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Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2021-12, Vol.23 (24), p.9870-9875 |
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container_title | Green chemistry : an international journal and green chemistry resource : GC |
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creator | Tang, Minhao Zhang, Fengtao Zhao, Yanfei Wang, Yuepeng Ke, Zhengang Li, Ruipeng Zeng, Wei Han, Buxing Liu, Zhimin |
description | Herein, we report a CO
2
-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO
2
(
e.g.
, azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO
2
could abstract one proton from proton resources (
e.g.
, IL cation) and transfer it to the CN or CC bonds
via
a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO
2
atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds
via
triple bond hydration under mild and metal-free conditions. |
doi_str_mv | 10.1039/D1GC03865F |
format | Article |
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2
-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO
2
(
e.g.
, azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO
2
could abstract one proton from proton resources (
e.g.
, IL cation) and transfer it to the CN or CC bonds
via
a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO
2
atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds
via
triple bond hydration under mild and metal-free conditions.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/D1GC03865F</identifier><language>eng</language><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2021-12, Vol.23 (24), p.9870-9875</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c76F-45e097957c449b823141fea7e0aba40645f12a2cec0e179adc4279bb8ac7419f3</citedby><cites>FETCH-LOGICAL-c76F-45e097957c449b823141fea7e0aba40645f12a2cec0e179adc4279bb8ac7419f3</cites><orcidid>0000-0001-7953-7414 ; 0000-0003-0440-809X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Tang, Minhao</creatorcontrib><creatorcontrib>Zhang, Fengtao</creatorcontrib><creatorcontrib>Zhao, Yanfei</creatorcontrib><creatorcontrib>Wang, Yuepeng</creatorcontrib><creatorcontrib>Ke, Zhengang</creatorcontrib><creatorcontrib>Li, Ruipeng</creatorcontrib><creatorcontrib>Zeng, Wei</creatorcontrib><creatorcontrib>Han, Buxing</creatorcontrib><creatorcontrib>Liu, Zhimin</creatorcontrib><title>A CO 2 -mediated base catalysis approach for the hydration of triple bonds in ionic liquids</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>Herein, we report a CO
2
-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO
2
(
e.g.
, azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO
2
could abstract one proton from proton resources (
e.g.
, IL cation) and transfer it to the CN or CC bonds
via
a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO
2
atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds
via
triple bond hydration under mild and metal-free conditions.</description><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFkL1OwzAYRS0EEqWw8ATfjBTwX-x4rAIpSJW6dGOIvvhHMUqTYIehbw8IBNO5OsMdDiG3jN4zKszDI9vWVFSqbM7IikklCsM1Pf_bil-Sq5zfKGVMK7kirxuo98ChOHoXcfEOOsweLC44nHLMgPOcJrQ9hCnB0nvoTy7hEqcRpgBLivPgoZtGlyGO8KWjhSG-f0SXr8lFwCH7m1-uyaF5OtTPxW6_fak3u8Jq1RSy9NRoU2orpekqLphkwaP2FDuUVMkyMI7ceks90wadlVybrqvQaslMEGty93Nr05Rz8qGdUzxiOrWMtt9V2v8q4hNPp1Qw</recordid><startdate>20211213</startdate><enddate>20211213</enddate><creator>Tang, Minhao</creator><creator>Zhang, Fengtao</creator><creator>Zhao, Yanfei</creator><creator>Wang, Yuepeng</creator><creator>Ke, Zhengang</creator><creator>Li, Ruipeng</creator><creator>Zeng, Wei</creator><creator>Han, Buxing</creator><creator>Liu, Zhimin</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-7953-7414</orcidid><orcidid>https://orcid.org/0000-0003-0440-809X</orcidid></search><sort><creationdate>20211213</creationdate><title>A CO 2 -mediated base catalysis approach for the hydration of triple bonds in ionic liquids</title><author>Tang, Minhao ; Zhang, Fengtao ; Zhao, Yanfei ; Wang, Yuepeng ; Ke, Zhengang ; Li, Ruipeng ; Zeng, Wei ; Han, Buxing ; Liu, Zhimin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c76F-45e097957c449b823141fea7e0aba40645f12a2cec0e179adc4279bb8ac7419f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tang, Minhao</creatorcontrib><creatorcontrib>Zhang, Fengtao</creatorcontrib><creatorcontrib>Zhao, Yanfei</creatorcontrib><creatorcontrib>Wang, Yuepeng</creatorcontrib><creatorcontrib>Ke, Zhengang</creatorcontrib><creatorcontrib>Li, Ruipeng</creatorcontrib><creatorcontrib>Zeng, Wei</creatorcontrib><creatorcontrib>Han, Buxing</creatorcontrib><creatorcontrib>Liu, Zhimin</creatorcontrib><collection>CrossRef</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tang, Minhao</au><au>Zhang, Fengtao</au><au>Zhao, Yanfei</au><au>Wang, Yuepeng</au><au>Ke, Zhengang</au><au>Li, Ruipeng</au><au>Zeng, Wei</au><au>Han, Buxing</au><au>Liu, Zhimin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A CO 2 -mediated base catalysis approach for the hydration of triple bonds in ionic liquids</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2021-12-13</date><risdate>2021</risdate><volume>23</volume><issue>24</issue><spage>9870</spage><epage>9875</epage><pages>9870-9875</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>Herein, we report a CO
2
-mediated base catalysis approach for the activation of triple bonds in ionic liquids (ILs) with anions that can chemically capture CO
2
(
e.g.
, azolate, phenolate, and acetate), which can achieve hydration of triple bonds to carbonyl chemicals. It is discovered that the anion-complexed CO
2
could abstract one proton from proton resources (
e.g.
, IL cation) and transfer it to the CN or CC bonds
via
a six-membered ring transition state, thus realizing their hydration. In particular, tetrabutylphosphonium 2-hydroxypyridine shows high efficiency for hydration of nitriles and CC bond-containing compounds under a CO
2
atmosphere, affording a series of carbonyl compounds in excellent yields. This catalytic protocol is simple, green, and highly efficient and opens a new way to access carbonyl compounds
via
triple bond hydration under mild and metal-free conditions.</abstract><doi>10.1039/D1GC03865F</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-7953-7414</orcidid><orcidid>https://orcid.org/0000-0003-0440-809X</orcidid></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
title | A CO 2 -mediated base catalysis approach for the hydration of triple bonds in ionic liquids |
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