Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling
Under the catalysis of PdBr 2 and a chiral phosphoramidite ligand, the upper-rim mono (2-bromoaroyl)-substituted calix[4]arene derivatives underwent a facile enantioselective desymmetrization reaction to afford 9 H -fluorene-embedded inherently chiral calixarenes in good yields with excellent enanti...
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| Veröffentlicht in: | Chemical science (Cambridge) 2023-01, Vol.14 (4), p.827-832 |
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| creator | Zhang, Xin Tong, Shuo Zhu, Jieping Wang, Mei-Xiang |
| description | Under the catalysis of PdBr
2
and a chiral phosphoramidite ligand, the upper-rim mono (2-bromoaroyl)-substituted calix[4]arene derivatives underwent a facile enantioselective desymmetrization reaction to afford 9
H
-fluorene-embedded inherently chiral calixarenes in good yields with excellent enantioselectivities. The transannular dehydrogenative arene-arene coupling reaction proceeded most probably through an oxidative addition of the C
aryl
-Br bond to a ligated palladium catalyst followed by a sequence of an enantioselective 1,5-palladium migration and an intramolecular C-H arylation sequence. This new family of inherently chiral calixarenes possesses unique chiroptical properties thanks to their highly rigid structure induced by the 9
H
-fluorene segment.
Reported here is the catalytic enantioselective desymmetrization of calixarene skeletons for the construction of inherently chiral calixarenes through a transannular arene-arene dehydrogenative coupling reaction. |
| doi_str_mv | 10.1039/d2sc06234h |
| format | Article |
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2
and a chiral phosphoramidite ligand, the upper-rim mono (2-bromoaroyl)-substituted calix[4]arene derivatives underwent a facile enantioselective desymmetrization reaction to afford 9
H
-fluorene-embedded inherently chiral calixarenes in good yields with excellent enantioselectivities. The transannular dehydrogenative arene-arene coupling reaction proceeded most probably through an oxidative addition of the C
aryl
-Br bond to a ligated palladium catalyst followed by a sequence of an enantioselective 1,5-palladium migration and an intramolecular C-H arylation sequence. This new family of inherently chiral calixarenes possesses unique chiroptical properties thanks to their highly rigid structure induced by the 9
H
-fluorene segment.
Reported here is the catalytic enantioselective desymmetrization of calixarene skeletons for the construction of inherently chiral calixarenes through a transannular arene-arene dehydrogenative coupling reaction.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/d2sc06234h</identifier><identifier>PMID: 36755707</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Calixarenes ; Catalysis ; Chemistry ; Coupling ; Dehydrogenation ; Enantiomers ; Palladium ; Rigid structures</subject><ispartof>Chemical science (Cambridge), 2023-01, Vol.14 (4), p.827-832</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c469t-e73b5e7572b87cd14d5481d91ba5072980578905dbdf9057e7f345bf37c3b0443</citedby><cites>FETCH-LOGICAL-c469t-e73b5e7572b87cd14d5481d91ba5072980578905dbdf9057e7f345bf37c3b0443</cites><orcidid>0000-0002-8390-6689 ; 0000-0001-7112-0657 ; 0000-0002-7982-2546</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9890570/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9890570/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36755707$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Xin</creatorcontrib><creatorcontrib>Tong, Shuo</creatorcontrib><creatorcontrib>Zhu, Jieping</creatorcontrib><creatorcontrib>Wang, Mei-Xiang</creatorcontrib><title>Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>Under the catalysis of PdBr
2
and a chiral phosphoramidite ligand, the upper-rim mono (2-bromoaroyl)-substituted calix[4]arene derivatives underwent a facile enantioselective desymmetrization reaction to afford 9
H
-fluorene-embedded inherently chiral calixarenes in good yields with excellent enantioselectivities. The transannular dehydrogenative arene-arene coupling reaction proceeded most probably through an oxidative addition of the C
aryl
-Br bond to a ligated palladium catalyst followed by a sequence of an enantioselective 1,5-palladium migration and an intramolecular C-H arylation sequence. This new family of inherently chiral calixarenes possesses unique chiroptical properties thanks to their highly rigid structure induced by the 9
H
-fluorene segment.
Reported here is the catalytic enantioselective desymmetrization of calixarene skeletons for the construction of inherently chiral calixarenes through a transannular arene-arene dehydrogenative coupling reaction.</description><subject>Calixarenes</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Coupling</subject><subject>Dehydrogenation</subject><subject>Enantiomers</subject><subject>Palladium</subject><subject>Rigid structures</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdks1r3DAQxUVoaUKaS-8Jhl5KwY2sD8u6FML2I4FAD2nPQpbGayWytZHsUPevr7KbbtPqMmLmx2OenhB6U-EPFaby3JJkcE0o6w_QEcGsKmtO5Yv9neBDdJLSLc6H0ooT8Qod0lpwLrA4QndXYw8Rxskvheld1L4w2rufOvcgFe1S6NyYtF8mZwoY9Ti5kMCDmdwDFBbSMgwwRffLjevCxJBSaaFfbAzrTG8hE-aNz-PX6GWnfYKTp3qMfnz5_H11WV5_-3q1urguDavlVIKgLQfBBWkbYWzFLGdNZWXVao4FkQ3mopGY29Z2uQgQHWW87agwtMWM0WP0cae7mdsBrMnusi-1iW7QcVFBO_XvZHS9WocHJR9lBc4C754EYrifIU1qcMmA93qEMCdFhGCNzCDP6Nv_0NswxzHby1TdSCkYl5l6v6O2DxSh2y9TYfUYo_pEblbbGC8zfPZ8_T36J7QMnO6AmMx--vcf0N-2q6SB</recordid><startdate>20230125</startdate><enddate>20230125</enddate><creator>Zhang, Xin</creator><creator>Tong, Shuo</creator><creator>Zhu, Jieping</creator><creator>Wang, Mei-Xiang</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-8390-6689</orcidid><orcidid>https://orcid.org/0000-0001-7112-0657</orcidid><orcidid>https://orcid.org/0000-0002-7982-2546</orcidid></search><sort><creationdate>20230125</creationdate><title>Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling</title><author>Zhang, Xin ; Tong, Shuo ; Zhu, Jieping ; Wang, Mei-Xiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c469t-e73b5e7572b87cd14d5481d91ba5072980578905dbdf9057e7f345bf37c3b0443</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Calixarenes</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Coupling</topic><topic>Dehydrogenation</topic><topic>Enantiomers</topic><topic>Palladium</topic><topic>Rigid structures</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xin</creatorcontrib><creatorcontrib>Tong, Shuo</creatorcontrib><creatorcontrib>Zhu, Jieping</creatorcontrib><creatorcontrib>Wang, Mei-Xiang</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>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Xin</au><au>Tong, Shuo</au><au>Zhu, Jieping</au><au>Wang, Mei-Xiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2023-01-25</date><risdate>2023</risdate><volume>14</volume><issue>4</issue><spage>827</spage><epage>832</epage><pages>827-832</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>Under the catalysis of PdBr
2
and a chiral phosphoramidite ligand, the upper-rim mono (2-bromoaroyl)-substituted calix[4]arene derivatives underwent a facile enantioselective desymmetrization reaction to afford 9
H
-fluorene-embedded inherently chiral calixarenes in good yields with excellent enantioselectivities. The transannular dehydrogenative arene-arene coupling reaction proceeded most probably through an oxidative addition of the C
aryl
-Br bond to a ligated palladium catalyst followed by a sequence of an enantioselective 1,5-palladium migration and an intramolecular C-H arylation sequence. This new family of inherently chiral calixarenes possesses unique chiroptical properties thanks to their highly rigid structure induced by the 9
H
-fluorene segment.
Reported here is the catalytic enantioselective desymmetrization of calixarene skeletons for the construction of inherently chiral calixarenes through a transannular arene-arene dehydrogenative coupling reaction.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36755707</pmid><doi>10.1039/d2sc06234h</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-8390-6689</orcidid><orcidid>https://orcid.org/0000-0001-7112-0657</orcidid><orcidid>https://orcid.org/0000-0002-7982-2546</orcidid><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | DOAJ Directory of Open Access Journals; EZB-FREE-00999 freely available EZB journals; PubMed Central; PubMed Central Open Access |
| subjects | Calixarenes Catalysis Chemistry Coupling Dehydrogenation Enantiomers Palladium Rigid structures |
| title | Inherently chiral calixarenes by a catalytic enantioselective desymmetrizing cross-dehydrogenative coupling |
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