Preparation of a novel cadmium-containing coordination polymer and catalytic application in the synthesis of N -alkylated aminoquinoline derivatives via the borrowing hydrogen approach
Herein, we report an efficient and straightforward approach for the synthesis of -alkylated aminoquinoline derivatives by recyclable Cd-containing coordination polymer-catalyzed reactions of aminoquinolines with primary alcohols the borrowing hydrogen strategy. In this work, a new type of coordinati...
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Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2024-03, Vol.53 (11), p.5064-5072 |
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container_title | Dalton transactions : an international journal of inorganic chemistry |
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creator | Li, Jiahao Mao, Anruo Hu, Xinyu Wang, Likui Wang, Dawei Duan, Zheng-Chao |
description | Herein, we report an efficient and straightforward approach for the synthesis of
-alkylated aminoquinoline derivatives by recyclable Cd-containing coordination polymer-catalyzed reactions of aminoquinolines with primary alcohols
the borrowing hydrogen strategy. In this work, a new type of coordination polymer [Cd(CIA)(phen)
(H
O)]
was successfully designed and fabricated. The molecular structure was corroborated by single-crystal X-ray diffraction and fully characterized by PXRD, FT-IR, TGA, and XPS. Importantly, this polymer revealed high catalytic activity for the
-alkylation reaction of 2-aminoquinoline and 8-aminoquinoline with inexpensive and low-toxicity alcohols as alkylating agents in excellent yields up to 95%. Interestingly, the present synthetic protocol was successfully applied for the gram-level synthesis of several biologically active compounds. In addition, several control reactions were carried out to investigate the possible mechanisms of this transformation. Finally, recycling experiments indicated that the cadmium coordination polymer showed good recovery performance for borrowing hydrogen reactions. |
doi_str_mv | 10.1039/d3dt04221a |
format | Article |
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-alkylated aminoquinoline derivatives by recyclable Cd-containing coordination polymer-catalyzed reactions of aminoquinolines with primary alcohols
the borrowing hydrogen strategy. In this work, a new type of coordination polymer [Cd(CIA)(phen)
(H
O)]
was successfully designed and fabricated. The molecular structure was corroborated by single-crystal X-ray diffraction and fully characterized by PXRD, FT-IR, TGA, and XPS. Importantly, this polymer revealed high catalytic activity for the
-alkylation reaction of 2-aminoquinoline and 8-aminoquinoline with inexpensive and low-toxicity alcohols as alkylating agents in excellent yields up to 95%. Interestingly, the present synthetic protocol was successfully applied for the gram-level synthesis of several biologically active compounds. In addition, several control reactions were carried out to investigate the possible mechanisms of this transformation. Finally, recycling experiments indicated that the cadmium coordination polymer showed good recovery performance for borrowing hydrogen reactions.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d3dt04221a</identifier><identifier>PMID: 38375833</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alcohols ; Alkylation ; Aminoquinolines ; Cadmium ; Catalytic activity ; Chemical reactions ; Chemical synthesis ; Coordination polymers ; Hydrogen ; Molecular structure ; Single crystals</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2024-03, Vol.53 (11), p.5064-5072</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c274t-9efafe73738da7506f59d7d4eba691a3eeeb5d50f32f43ca5644d2242f9b02103</cites><orcidid>0000-0002-9774-9258 ; 0000-0001-9327-7487</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38375833$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Jiahao</creatorcontrib><creatorcontrib>Mao, Anruo</creatorcontrib><creatorcontrib>Hu, Xinyu</creatorcontrib><creatorcontrib>Wang, Likui</creatorcontrib><creatorcontrib>Wang, Dawei</creatorcontrib><creatorcontrib>Duan, Zheng-Chao</creatorcontrib><title>Preparation of a novel cadmium-containing coordination polymer and catalytic application in the synthesis of N -alkylated aminoquinoline derivatives via the borrowing hydrogen approach</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>Herein, we report an efficient and straightforward approach for the synthesis of
-alkylated aminoquinoline derivatives by recyclable Cd-containing coordination polymer-catalyzed reactions of aminoquinolines with primary alcohols
the borrowing hydrogen strategy. In this work, a new type of coordination polymer [Cd(CIA)(phen)
(H
O)]
was successfully designed and fabricated. The molecular structure was corroborated by single-crystal X-ray diffraction and fully characterized by PXRD, FT-IR, TGA, and XPS. Importantly, this polymer revealed high catalytic activity for the
-alkylation reaction of 2-aminoquinoline and 8-aminoquinoline with inexpensive and low-toxicity alcohols as alkylating agents in excellent yields up to 95%. Interestingly, the present synthetic protocol was successfully applied for the gram-level synthesis of several biologically active compounds. In addition, several control reactions were carried out to investigate the possible mechanisms of this transformation. Finally, recycling experiments indicated that the cadmium coordination polymer showed good recovery performance for borrowing hydrogen reactions.</description><subject>Alcohols</subject><subject>Alkylation</subject><subject>Aminoquinolines</subject><subject>Cadmium</subject><subject>Catalytic activity</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Coordination polymers</subject><subject>Hydrogen</subject><subject>Molecular structure</subject><subject>Single crystals</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkc1u1TAQhS1ERUthwwMgS2yqSimOHednWbUUkKrCoqyjiT3udXHs1E4uypvxePXtLV2wmZnFN-eM5hDyoWRnJRPdZy30zCrOS3hFjsqqaYqOi-r1y8zrQ_I2pXvGOGeSvyGHohWNbIU4In9_RpwgwmyDp8FQoD5s0VEFerTLWKjgZ7De-juqQoja-j06BbeOGCl4ndkZ3DpbRWGanFV7wno6b5Cm1eeWbNqp39AC3O_VwYyawmh9eFhycdYj1RjtNq9uMdGthaflIcQY_uzMN6uO4Q79ziIGUJt35MCAS_j-uR-TX1dfbi--Fdc_vn6_OL8uFG-quejQgMFGNKLV0EhWG9npRlc4QN2VIBBxkFoyI7iphAJZV5XmvOKmGxjP7z0mJ3vdbPuwYJr70SaFzoHHsKSed7xtpSibOqOf_kPvwxJ9vi5TUmY1WXaZOt1TKoaUIpp-inaEuPYl63d59pfi8vYpz_MMf3yWXIYR9Qv6L0DxCAoMoCQ</recordid><startdate>20240312</startdate><enddate>20240312</enddate><creator>Li, Jiahao</creator><creator>Mao, Anruo</creator><creator>Hu, Xinyu</creator><creator>Wang, Likui</creator><creator>Wang, Dawei</creator><creator>Duan, Zheng-Chao</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9774-9258</orcidid><orcidid>https://orcid.org/0000-0001-9327-7487</orcidid></search><sort><creationdate>20240312</creationdate><title>Preparation of a novel cadmium-containing coordination polymer and catalytic application in the synthesis of N -alkylated aminoquinoline derivatives via the borrowing hydrogen approach</title><author>Li, Jiahao ; Mao, Anruo ; Hu, Xinyu ; Wang, Likui ; Wang, Dawei ; Duan, Zheng-Chao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c274t-9efafe73738da7506f59d7d4eba691a3eeeb5d50f32f43ca5644d2242f9b02103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alcohols</topic><topic>Alkylation</topic><topic>Aminoquinolines</topic><topic>Cadmium</topic><topic>Catalytic activity</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Coordination polymers</topic><topic>Hydrogen</topic><topic>Molecular structure</topic><topic>Single crystals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jiahao</creatorcontrib><creatorcontrib>Mao, Anruo</creatorcontrib><creatorcontrib>Hu, Xinyu</creatorcontrib><creatorcontrib>Wang, Likui</creatorcontrib><creatorcontrib>Wang, Dawei</creatorcontrib><creatorcontrib>Duan, Zheng-Chao</creatorcontrib><collection>PubMed</collection><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><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Jiahao</au><au>Mao, Anruo</au><au>Hu, Xinyu</au><au>Wang, Likui</au><au>Wang, Dawei</au><au>Duan, Zheng-Chao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of a novel cadmium-containing coordination polymer and catalytic application in the synthesis of N -alkylated aminoquinoline derivatives via the borrowing hydrogen approach</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2024-03-12</date><risdate>2024</risdate><volume>53</volume><issue>11</issue><spage>5064</spage><epage>5072</epage><pages>5064-5072</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>Herein, we report an efficient and straightforward approach for the synthesis of
-alkylated aminoquinoline derivatives by recyclable Cd-containing coordination polymer-catalyzed reactions of aminoquinolines with primary alcohols
the borrowing hydrogen strategy. In this work, a new type of coordination polymer [Cd(CIA)(phen)
(H
O)]
was successfully designed and fabricated. The molecular structure was corroborated by single-crystal X-ray diffraction and fully characterized by PXRD, FT-IR, TGA, and XPS. Importantly, this polymer revealed high catalytic activity for the
-alkylation reaction of 2-aminoquinoline and 8-aminoquinoline with inexpensive and low-toxicity alcohols as alkylating agents in excellent yields up to 95%. Interestingly, the present synthetic protocol was successfully applied for the gram-level synthesis of several biologically active compounds. In addition, several control reactions were carried out to investigate the possible mechanisms of this transformation. Finally, recycling experiments indicated that the cadmium coordination polymer showed good recovery performance for borrowing hydrogen reactions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38375833</pmid><doi>10.1039/d3dt04221a</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-9774-9258</orcidid><orcidid>https://orcid.org/0000-0001-9327-7487</orcidid></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Alcohols Alkylation Aminoquinolines Cadmium Catalytic activity Chemical reactions Chemical synthesis Coordination polymers Hydrogen Molecular structure Single crystals |
title | Preparation of a novel cadmium-containing coordination polymer and catalytic application in the synthesis of N -alkylated aminoquinoline derivatives via the borrowing hydrogen approach |
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