Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling-alkyne semi-hydrogenation reactions
A series of heterobimetallic Pd /M complexes (M = Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling-alkyne semi-hydrogenation reactions to form -aryl alkenes. The carbometalated heterobimetallic Pd /Co complex CoPdL3' demonstrated an apparent cooperative ef...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2022-01, Vol.51 (4), p.1344-1356 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Clauss, Reike Baweja, Saral Gelman, Dmitri Hey-Hawkins, Evamarie |
| description | A series of heterobimetallic Pd
/M
complexes (M
= Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling-alkyne semi-hydrogenation reactions to form
-aryl alkenes. The carbometalated heterobimetallic Pd
/Co
complex CoPdL3' demonstrated an apparent cooperative effect compared to the corresponding monometallic counterparts. This compound was identified as a potent single-molecule catalyst for the one-pot Cu-free Sonogashira coupling of aryl bromides with terminal alkynes followed by chemo- and stereoselective semi-hydrogenation of the alkyne intermediate using NH
·BH
as a hydrogen source. Furthermore, different aromatic substrates have been tested to show the generality of the reaction for the synthesis of
-alkenes, including biologically active combretastatin A-4. In addition, the homogeneous nature of the catalytically active species was demonstrated. |
| doi_str_mv | 10.1039/d1dt03757a |
| format | Article |
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/M
complexes (M
= Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling-alkyne semi-hydrogenation reactions to form
-aryl alkenes. The carbometalated heterobimetallic Pd
/Co
complex CoPdL3' demonstrated an apparent cooperative effect compared to the corresponding monometallic counterparts. This compound was identified as a potent single-molecule catalyst for the one-pot Cu-free Sonogashira coupling of aryl bromides with terminal alkynes followed by chemo- and stereoselective semi-hydrogenation of the alkyne intermediate using NH
·BH
as a hydrogen source. Furthermore, different aromatic substrates have been tested to show the generality of the reaction for the synthesis of
-alkenes, including biologically active combretastatin A-4. In addition, the homogeneous nature of the catalytically active species was demonstrated.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d1dt03757a</identifier><identifier>PMID: 34889939</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkenes ; Alkynes ; Ammonia ; Aromatic compounds ; Bromides ; Catalysts ; Chemical synthesis ; Cobalt ; Copper ; Coupling ; Hydrogenation ; Palladium ; Stereoselectivity ; Substrates</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2022-01, Vol.51 (4), p.1344-1356</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-2ff42dfc5603fb1c8bfb8647ba6b7dcc9f5bd85b503d50031f988a83aef550b3</citedby><cites>FETCH-LOGICAL-c315t-2ff42dfc5603fb1c8bfb8647ba6b7dcc9f5bd85b503d50031f988a83aef550b3</cites><orcidid>0000-0003-0370-7944 ; 0000-0003-4267-0603 ; 0000-0003-1380-2582 ; 0000-0001-7185-1345</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34889939$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Clauss, Reike</creatorcontrib><creatorcontrib>Baweja, Saral</creatorcontrib><creatorcontrib>Gelman, Dmitri</creatorcontrib><creatorcontrib>Hey-Hawkins, Evamarie</creatorcontrib><title>Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling-alkyne semi-hydrogenation reactions</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>A series of heterobimetallic Pd
/M
complexes (M
= Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling-alkyne semi-hydrogenation reactions to form
-aryl alkenes. The carbometalated heterobimetallic Pd
/Co
complex CoPdL3' demonstrated an apparent cooperative effect compared to the corresponding monometallic counterparts. This compound was identified as a potent single-molecule catalyst for the one-pot Cu-free Sonogashira coupling of aryl bromides with terminal alkynes followed by chemo- and stereoselective semi-hydrogenation of the alkyne intermediate using NH
·BH
as a hydrogen source. Furthermore, different aromatic substrates have been tested to show the generality of the reaction for the synthesis of
-alkenes, including biologically active combretastatin A-4. In addition, the homogeneous nature of the catalytically active species was demonstrated.</description><subject>Alkenes</subject><subject>Alkynes</subject><subject>Ammonia</subject><subject>Aromatic compounds</subject><subject>Bromides</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Cobalt</subject><subject>Copper</subject><subject>Coupling</subject><subject>Hydrogenation</subject><subject>Palladium</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpd0ctu1DAYBeAIgegFNjwAssQGVUrrS5w4y2oKFKmolZh95MvvqYtjD7ZTMQ_Ee9bTli5Y-Sw-H_3SaZoPBJ8SzMYzQ0zBbOCDfNUckm4Y2pGy7vVLpv1Bc5TzHcaUYk7fNgesE2Ic2XjY_L2EAikqN0OR3juNbszZj4BkMPu0ikjHeevhD2QkMwJrnXYQyiPI9SvEDB50cfeAtKwdu1wysjGhDL-XKp30aLW0NgGgnzHEjcy3Lsnau2y9C5tW-l-7AJXPrr3dmRQ3EGRxMaAEUu9Dfte8sdJneP_8Hjfrr1_Wq8v26vrb99X5VasZ4aWl1nbUWM17zKwiWiirRN8NSvZqMFqPlisjuOKYGY4xI3YUQgomwXKOFTtuPj_VblOst-cyzS5r8F4GiEueaI8FZ0PH-ko__Ufv4pJCPa4qyjDtBeVVnTwpnWLOCey0TW6WaTcRPO23my7Ixfpxu_OKPz5XLmoG80L_jcUeAHDwmJw</recordid><startdate>20220125</startdate><enddate>20220125</enddate><creator>Clauss, Reike</creator><creator>Baweja, Saral</creator><creator>Gelman, Dmitri</creator><creator>Hey-Hawkins, Evamarie</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/0000-0003-0370-7944</orcidid><orcidid>https://orcid.org/0000-0003-4267-0603</orcidid><orcidid>https://orcid.org/0000-0003-1380-2582</orcidid><orcidid>https://orcid.org/0000-0001-7185-1345</orcidid></search><sort><creationdate>20220125</creationdate><title>Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling-alkyne semi-hydrogenation reactions</title><author>Clauss, Reike ; Baweja, Saral ; Gelman, Dmitri ; Hey-Hawkins, Evamarie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-2ff42dfc5603fb1c8bfb8647ba6b7dcc9f5bd85b503d50031f988a83aef550b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkenes</topic><topic>Alkynes</topic><topic>Ammonia</topic><topic>Aromatic compounds</topic><topic>Bromides</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Cobalt</topic><topic>Copper</topic><topic>Coupling</topic><topic>Hydrogenation</topic><topic>Palladium</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Clauss, Reike</creatorcontrib><creatorcontrib>Baweja, Saral</creatorcontrib><creatorcontrib>Gelman, Dmitri</creatorcontrib><creatorcontrib>Hey-Hawkins, Evamarie</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>Clauss, Reike</au><au>Baweja, Saral</au><au>Gelman, Dmitri</au><au>Hey-Hawkins, Evamarie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling-alkyne semi-hydrogenation reactions</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2022-01-25</date><risdate>2022</risdate><volume>51</volume><issue>4</issue><spage>1344</spage><epage>1356</epage><pages>1344-1356</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>A series of heterobimetallic Pd
/M
complexes (M
= Mn, Co) were synthesised and tested as precatalysts for sequential Sonogashira coupling-alkyne semi-hydrogenation reactions to form
-aryl alkenes. The carbometalated heterobimetallic Pd
/Co
complex CoPdL3' demonstrated an apparent cooperative effect compared to the corresponding monometallic counterparts. This compound was identified as a potent single-molecule catalyst for the one-pot Cu-free Sonogashira coupling of aryl bromides with terminal alkynes followed by chemo- and stereoselective semi-hydrogenation of the alkyne intermediate using NH
·BH
as a hydrogen source. Furthermore, different aromatic substrates have been tested to show the generality of the reaction for the synthesis of
-alkenes, including biologically active combretastatin A-4. In addition, the homogeneous nature of the catalytically active species was demonstrated.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34889939</pmid><doi>10.1039/d1dt03757a</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0003-0370-7944</orcidid><orcidid>https://orcid.org/0000-0003-4267-0603</orcidid><orcidid>https://orcid.org/0000-0003-1380-2582</orcidid><orcidid>https://orcid.org/0000-0001-7185-1345</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2022-01, Vol.51 (4), p.1344-1356 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2608537436 |
| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Alkenes Alkynes Ammonia Aromatic compounds Bromides Catalysts Chemical synthesis Cobalt Copper Coupling Hydrogenation Palladium Stereoselectivity Substrates |
| title | Heterobimetallic Pd/Mn and Pd/Co complexes as efficient and stereoselective catalysts for sequential Cu-free Sonogashira coupling-alkyne semi-hydrogenation reactions |
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