Expedient Synthesis of Dihaloalkenynes via Pd‐Catalyzed Haloalkynylation Reaction
Herein, the PdII‐catalyzed construction of functionalized dihaloalkenynes from haloalkynes via a self‐haloalkynylation reaction, without specialized ligands or oxidizing additives, is reported. The method tolerates a diverse range of haloalkynes, including electron‐donating and electron‐withdrawing...
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| Veröffentlicht in: | Chemistry : a European journal 2023-05, Vol.29 (26), p.e202300068-n/a |
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| creator | Ji, Xiaoliang Peng, Xin Hong, Huanliang Xu, Yanghao Nie, Jinli Chen, Lu Mo, Zongwen Li, Yibiao Jiang, Huanfeng |
| description | Herein, the PdII‐catalyzed construction of functionalized dihaloalkenynes from haloalkynes via a self‐haloalkynylation reaction, without specialized ligands or oxidizing additives, is reported. The method tolerates a diverse range of haloalkynes, including electron‐donating and electron‐withdrawing functional groups, such as macrocyclic alkynols, spiro‐oxy ring alkynols, and even carbazole‐containing, pyrrolidine‐2,5‐dione‐containing and silyl‐protected bromoalkynes. Using an opposite lithium halide (LiX) to the haloalkyne starting material, remarkably high regio‐ and stereoselectivity of the haloalkynylation reaction is possible, yielding 1‐bromo‐2‐chloroalkenyne or 2‐bromo‐1‐chloroalkenyne products as desired.
A robust and regioselective PdII‐catalyzed haloalkynylation of haloalkynes has been established under ligand‐free and oxidant‐free conditions. Careful selection of the haloalkyne starting material, with respect to electron densities of the alkyne, allows for strong control of the order and selectivity of the halide atoms in the coupled product. |
| doi_str_mv | 10.1002/chem.202300068 |
| format | Article |
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A robust and regioselective PdII‐catalyzed haloalkynylation of haloalkynes has been established under ligand‐free and oxidant‐free conditions. Careful selection of the haloalkyne starting material, with respect to electron densities of the alkyne, allows for strong control of the order and selectivity of the halide atoms in the coupled product.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202300068</identifier><identifier>PMID: 36797659</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Additives ; Carbazole ; Carbazoles ; Chemical synthesis ; Chemistry ; dihaloalkane ; Functional groups ; haloalkyne ; haloalkynylation ; halopalladation ; Lithium ; Oxidation ; palladium ; Pyrrolidine ; Stereoselectivity</subject><ispartof>Chemistry : a European journal, 2023-05, Vol.29 (26), p.e202300068-n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2023 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3738-e5c06d07e615f796e8db2f68dbde50a316715a7e5886e829fc16cf8e3517e9d13</citedby><cites>FETCH-LOGICAL-c3738-e5c06d07e615f796e8db2f68dbde50a316715a7e5886e829fc16cf8e3517e9d13</cites><orcidid>0000-0001-8249-5630</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%2Fchem.202300068$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202300068$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36797659$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ji, Xiaoliang</creatorcontrib><creatorcontrib>Peng, Xin</creatorcontrib><creatorcontrib>Hong, Huanliang</creatorcontrib><creatorcontrib>Xu, Yanghao</creatorcontrib><creatorcontrib>Nie, Jinli</creatorcontrib><creatorcontrib>Chen, Lu</creatorcontrib><creatorcontrib>Mo, Zongwen</creatorcontrib><creatorcontrib>Li, Yibiao</creatorcontrib><creatorcontrib>Jiang, Huanfeng</creatorcontrib><title>Expedient Synthesis of Dihaloalkenynes via Pd‐Catalyzed Haloalkynylation Reaction</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Herein, the PdII‐catalyzed construction of functionalized dihaloalkenynes from haloalkynes via a self‐haloalkynylation reaction, without specialized ligands or oxidizing additives, is reported. The method tolerates a diverse range of haloalkynes, including electron‐donating and electron‐withdrawing functional groups, such as macrocyclic alkynols, spiro‐oxy ring alkynols, and even carbazole‐containing, pyrrolidine‐2,5‐dione‐containing and silyl‐protected bromoalkynes. Using an opposite lithium halide (LiX) to the haloalkyne starting material, remarkably high regio‐ and stereoselectivity of the haloalkynylation reaction is possible, yielding 1‐bromo‐2‐chloroalkenyne or 2‐bromo‐1‐chloroalkenyne products as desired.
A robust and regioselective PdII‐catalyzed haloalkynylation of haloalkynes has been established under ligand‐free and oxidant‐free conditions. Careful selection of the haloalkyne starting material, with respect to electron densities of the alkyne, allows for strong control of the order and selectivity of the halide atoms in the coupled product.</description><subject>Additives</subject><subject>Carbazole</subject><subject>Carbazoles</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>dihaloalkane</subject><subject>Functional groups</subject><subject>haloalkyne</subject><subject>haloalkynylation</subject><subject>halopalladation</subject><subject>Lithium</subject><subject>Oxidation</subject><subject>palladium</subject><subject>Pyrrolidine</subject><subject>Stereoselectivity</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqF0LtOwzAUBmALgWgprIwoEgtLii-1HY8oFIpUBKIwW25yoqbkUuIECBOPwDPyJLhKAYmFxbbk7_w6-hE6JHhIMKan0QLyIcWUYYxFsIX6hFPiMyn4NupjNZK-4Ez10J61S0eUYGwX9ZiQyhHVR7Px6wriFIram7VFvQCbWq9MvPN0YbLSZI9QtAVY7zk13m38-f4Rmtpk7RvE3qQDbdFmpk7LwrsDE60f-2gnMZmFg809QA8X4_tw4k9vLq_Cs6kfMckCH3iERYwlCMITqQQE8Zwmwp0xcGwYEZJwI4EHgfujKomIiJIAGCcSVEzYAJ10uauqfGrA1jpPbQRZZgooG6upVBhzTKV09PgPXZZNVbjtNA0IwYKPFHVq2KmoKq2tINGrKs1N1WqC9bpuva5b_9TtBo42sc08h_iHf_frgOrAS5pB-0-cDifj69_wL_RAjPo</recordid><startdate>20230508</startdate><enddate>20230508</enddate><creator>Ji, Xiaoliang</creator><creator>Peng, Xin</creator><creator>Hong, Huanliang</creator><creator>Xu, Yanghao</creator><creator>Nie, Jinli</creator><creator>Chen, Lu</creator><creator>Mo, Zongwen</creator><creator>Li, Yibiao</creator><creator>Jiang, Huanfeng</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8249-5630</orcidid></search><sort><creationdate>20230508</creationdate><title>Expedient Synthesis of Dihaloalkenynes via Pd‐Catalyzed Haloalkynylation Reaction</title><author>Ji, Xiaoliang ; Peng, Xin ; Hong, Huanliang ; Xu, Yanghao ; Nie, Jinli ; Chen, Lu ; Mo, Zongwen ; Li, Yibiao ; Jiang, Huanfeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3738-e5c06d07e615f796e8db2f68dbde50a316715a7e5886e829fc16cf8e3517e9d13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Additives</topic><topic>Carbazole</topic><topic>Carbazoles</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>dihaloalkane</topic><topic>Functional groups</topic><topic>haloalkyne</topic><topic>haloalkynylation</topic><topic>halopalladation</topic><topic>Lithium</topic><topic>Oxidation</topic><topic>palladium</topic><topic>Pyrrolidine</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ji, Xiaoliang</creatorcontrib><creatorcontrib>Peng, Xin</creatorcontrib><creatorcontrib>Hong, Huanliang</creatorcontrib><creatorcontrib>Xu, Yanghao</creatorcontrib><creatorcontrib>Nie, Jinli</creatorcontrib><creatorcontrib>Chen, Lu</creatorcontrib><creatorcontrib>Mo, Zongwen</creatorcontrib><creatorcontrib>Li, Yibiao</creatorcontrib><creatorcontrib>Jiang, Huanfeng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ji, Xiaoliang</au><au>Peng, Xin</au><au>Hong, Huanliang</au><au>Xu, Yanghao</au><au>Nie, Jinli</au><au>Chen, Lu</au><au>Mo, Zongwen</au><au>Li, Yibiao</au><au>Jiang, Huanfeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Expedient Synthesis of Dihaloalkenynes via Pd‐Catalyzed Haloalkynylation Reaction</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2023-05-08</date><risdate>2023</risdate><volume>29</volume><issue>26</issue><spage>e202300068</spage><epage>n/a</epage><pages>e202300068-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Herein, the PdII‐catalyzed construction of functionalized dihaloalkenynes from haloalkynes via a self‐haloalkynylation reaction, without specialized ligands or oxidizing additives, is reported. The method tolerates a diverse range of haloalkynes, including electron‐donating and electron‐withdrawing functional groups, such as macrocyclic alkynols, spiro‐oxy ring alkynols, and even carbazole‐containing, pyrrolidine‐2,5‐dione‐containing and silyl‐protected bromoalkynes. Using an opposite lithium halide (LiX) to the haloalkyne starting material, remarkably high regio‐ and stereoselectivity of the haloalkynylation reaction is possible, yielding 1‐bromo‐2‐chloroalkenyne or 2‐bromo‐1‐chloroalkenyne products as desired.
A robust and regioselective PdII‐catalyzed haloalkynylation of haloalkynes has been established under ligand‐free and oxidant‐free conditions. Careful selection of the haloalkyne starting material, with respect to electron densities of the alkyne, allows for strong control of the order and selectivity of the halide atoms in the coupled product.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36797659</pmid><doi>10.1002/chem.202300068</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-8249-5630</orcidid></addata></record> |
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| subjects | Additives Carbazole Carbazoles Chemical synthesis Chemistry dihaloalkane Functional groups haloalkyne haloalkynylation halopalladation Lithium Oxidation palladium Pyrrolidine Stereoselectivity |
| title | Expedient Synthesis of Dihaloalkenynes via Pd‐Catalyzed Haloalkynylation Reaction |
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