Pd( ii ) complexes with amide-based macrocycles: syntheses, properties and applications in cross-coupling reactions
This work shows Pd( ii ) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e − -donating and e − -withdrawing substituents on the ligand framework. Ligands constitute a N 4 square-planar cavity and optimally house the Pd( ii ) ion. The solution-state struct...
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| Veröffentlicht in: | New journal of chemistry 2015-01, Vol.39 (3), p.2042-2051 |
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| container_title | New journal of chemistry |
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| creator | Kumar, Sushil Jha, Rajeev Ranjan Yadav, Sunil Gupta, Rajeev |
| description | This work shows Pd(
ii
) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e
−
-donating and e
−
-withdrawing substituents on the ligand framework. Ligands constitute a N
4
square-planar cavity and optimally house the Pd(
ii
) ion. The solution-state structure
via
NMR and absorption spectra substantiates the solid-state structure obtained by crystallography. The electrochemical studies display the impact of electronic substituents on ligands that significantly influence the redox properties and also shift the locus of oxidation. These complexes were used in the Suzuki and Heck cross-coupling reactions. The moderate cross-coupling reaction results are due to limited redox accessibility that can be improved either by using substrates with a better leaving group or by placing electron-withdrawing substituents on the macrocyclic ligands. |
| doi_str_mv | 10.1039/C4NJ01300J |
| format | Article |
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ii
) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e
−
-donating and e
−
-withdrawing substituents on the ligand framework. Ligands constitute a N
4
square-planar cavity and optimally house the Pd(
ii
) ion. The solution-state structure
via
NMR and absorption spectra substantiates the solid-state structure obtained by crystallography. The electrochemical studies display the impact of electronic substituents on ligands that significantly influence the redox properties and also shift the locus of oxidation. These complexes were used in the Suzuki and Heck cross-coupling reactions. The moderate cross-coupling reaction results are due to limited redox accessibility that can be improved either by using substrates with a better leaving group or by placing electron-withdrawing substituents on the macrocyclic ligands.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/C4NJ01300J</identifier><language>eng</language><ispartof>New journal of chemistry, 2015-01, Vol.39 (3), p.2042-2051</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c231t-d4a51ac2cb69d6d717d32211757c1815898047c12f42424c7fcf0334472f938e3</citedby><cites>FETCH-LOGICAL-c231t-d4a51ac2cb69d6d717d32211757c1815898047c12f42424c7fcf0334472f938e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Kumar, Sushil</creatorcontrib><creatorcontrib>Jha, Rajeev Ranjan</creatorcontrib><creatorcontrib>Yadav, Sunil</creatorcontrib><creatorcontrib>Gupta, Rajeev</creatorcontrib><title>Pd( ii ) complexes with amide-based macrocycles: syntheses, properties and applications in cross-coupling reactions</title><title>New journal of chemistry</title><description>This work shows Pd(
ii
) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e
−
-donating and e
−
-withdrawing substituents on the ligand framework. Ligands constitute a N
4
square-planar cavity and optimally house the Pd(
ii
) ion. The solution-state structure
via
NMR and absorption spectra substantiates the solid-state structure obtained by crystallography. The electrochemical studies display the impact of electronic substituents on ligands that significantly influence the redox properties and also shift the locus of oxidation. These complexes were used in the Suzuki and Heck cross-coupling reactions. The moderate cross-coupling reaction results are due to limited redox accessibility that can be improved either by using substrates with a better leaving group or by placing electron-withdrawing substituents on the macrocyclic ligands.</description><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNpFUMtKBDEQDKLgunrxC3JUMZpOMo94k8HXsqgHPQ_ZTsaNzItkRPfvjasgfaiiimqKIuQY-AVwqS8r9bjgIDlf7JAZyFwzLXLYTRyUYjxT-T45iPGdc4AihxmJz_aEek9PKQ7d2LovF-mnn9bUdN46tjLRWdoZDANusHXxisZNP61ddPGcjmEYXZh8ypjeUjOOrUcz-aGP1Pc0hWJkOHwkuX-jwRnceodkrzFtdEd_OCevtzcv1T1bPt09VNdLhkLCxKwyGRgUuMq1zW0BhZVCpN5ZgVBCVuqSq0RFo0Q6LBpsuJRKFaLRsnRyTs5-_26LBNfUY_CdCZsaeP0zV_0_l_wGPoNdtA</recordid><startdate>20150101</startdate><enddate>20150101</enddate><creator>Kumar, Sushil</creator><creator>Jha, Rajeev Ranjan</creator><creator>Yadav, Sunil</creator><creator>Gupta, Rajeev</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150101</creationdate><title>Pd( ii ) complexes with amide-based macrocycles: syntheses, properties and applications in cross-coupling reactions</title><author>Kumar, Sushil ; Jha, Rajeev Ranjan ; Yadav, Sunil ; Gupta, Rajeev</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c231t-d4a51ac2cb69d6d717d32211757c1815898047c12f42424c7fcf0334472f938e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumar, Sushil</creatorcontrib><creatorcontrib>Jha, Rajeev Ranjan</creatorcontrib><creatorcontrib>Yadav, Sunil</creatorcontrib><creatorcontrib>Gupta, Rajeev</creatorcontrib><collection>CrossRef</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumar, Sushil</au><au>Jha, Rajeev Ranjan</au><au>Yadav, Sunil</au><au>Gupta, Rajeev</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pd( ii ) complexes with amide-based macrocycles: syntheses, properties and applications in cross-coupling reactions</atitle><jtitle>New journal of chemistry</jtitle><date>2015-01-01</date><risdate>2015</risdate><volume>39</volume><issue>3</issue><spage>2042</spage><epage>2051</epage><pages>2042-2051</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>This work shows Pd(
ii
) complexes in a set of 13-membered amide-based macrocyclic ligands varied by the placement of e
−
-donating and e
−
-withdrawing substituents on the ligand framework. Ligands constitute a N
4
square-planar cavity and optimally house the Pd(
ii
) ion. The solution-state structure
via
NMR and absorption spectra substantiates the solid-state structure obtained by crystallography. The electrochemical studies display the impact of electronic substituents on ligands that significantly influence the redox properties and also shift the locus of oxidation. These complexes were used in the Suzuki and Heck cross-coupling reactions. The moderate cross-coupling reaction results are due to limited redox accessibility that can be improved either by using substrates with a better leaving group or by placing electron-withdrawing substituents on the macrocyclic ligands.</abstract><doi>10.1039/C4NJ01300J</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2015-01, Vol.39 (3), p.2042-2051 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_C4NJ01300J |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Pd( ii ) complexes with amide-based macrocycles: syntheses, properties and applications in cross-coupling reactions |
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