Highly active mesoionic chalcogenone zinc() derivatives for C-S cross-coupling reactions
The first mesoionic heavier chalcogenones, L 1 -L 3 [ L 1 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone; L 2 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione; L 3 = 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used...
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creator | Vaddamanu, Moulali Velappan, Kavitha Prabusankar, Ganesan |
description | The first mesoionic heavier chalcogenones,
L
1
-L
3
[
L
1
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone;
L
2
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione;
L
3
= 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(
ii
) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(
ii
) chalcogenone complexes, [(
L
1
)Zn(Cl)
2
(HOMe)] (
1
), [(
L
2
)Zn(Cl)
2
(HOMe)] (
3
) and [(
L
2
)Zn(Br)
2
(HOMe)] (
4
), and two dinuclear zinc complexes, [(
L
1
)Zn(Br)(μ
2
-Br)]
2
(
2
) and [(
L
3
)Zn(Br)(μ
2
-Br)]
2
(
5
), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes
1-5
represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(
ii
) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.
Mesoionic heavier chalcogenone complexes of zinc(
ii
) have been isolated and utilized as catalysts in C-S cross coupling reactions between thiophenols and aryl halides under convenient reaction conditions. |
doi_str_mv | 10.1039/c9nj04440j |
format | Article |
fullrecord | <record><control><sourceid>proquest_rsc_p</sourceid><recordid>TN_cdi_rsc_primary_c9nj04440j</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2326928097</sourcerecordid><originalsourceid>FETCH-LOGICAL-c281t-63e7b93c49ca90972c0631adf1ba1dd98ee3347f4b5e71909a2914a39657196a3</originalsourceid><addsrcrecordid>eNpF0MFLwzAUBvAgCs7pxbsQ8KJCNS_J0uUoRZ1j6EEFbyVL0y2lS2bSDeZfb7aJnvICP773-BA6B3ILhMk7LV1DOOekOUA9YEJmkgo4TDNwnpEBF8foJMaGEIBcQA99juxs3m6w0p1dG7ww0VvvrMZ6rlrtZ8Z5Z_C3dfrqGlcm2LXawohrH3CRvWEdfIyZ9qtla90MB7NN8i6eoqNatdGc_b599PH48F6Mssnr03NxP8k0HUKXCWbyqWSaS60kkTnVRDBQVQ1TBVUlh8YwxvOaTwcmhyQUlcAVk2KQvkKxPrrc5y6D_1qZ2JWNXwWXVpaUUSHpMKUmdbNXu3ODqctlsAsVNiWQcttcWciX8a65ccIXexyi_nP_zbIfdz1qVg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2326928097</pqid></control><display><type>article</type><title>Highly active mesoionic chalcogenone zinc() derivatives for C-S cross-coupling reactions</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Vaddamanu, Moulali ; Velappan, Kavitha ; Prabusankar, Ganesan</creator><creatorcontrib>Vaddamanu, Moulali ; Velappan, Kavitha ; Prabusankar, Ganesan</creatorcontrib><description>The first mesoionic heavier chalcogenones,
L
1
-L
3
[
L
1
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone;
L
2
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione;
L
3
= 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(
ii
) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(
ii
) chalcogenone complexes, [(
L
1
)Zn(Cl)
2
(HOMe)] (
1
), [(
L
2
)Zn(Cl)
2
(HOMe)] (
3
) and [(
L
2
)Zn(Br)
2
(HOMe)] (
4
), and two dinuclear zinc complexes, [(
L
1
)Zn(Br)(μ
2
-Br)]
2
(
2
) and [(
L
3
)Zn(Br)(μ
2
-Br)]
2
(
5
), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes
1-5
represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(
ii
) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.
Mesoionic heavier chalcogenone complexes of zinc(
ii
) have been isolated and utilized as catalysts in C-S cross coupling reactions between thiophenols and aryl halides under convenient reaction conditions.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/c9nj04440j</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Chemical reactions ; Cross coupling ; Crystal structure ; Crystallography ; Crystals ; Density functional theory ; Derivatives ; Halides ; Ligands ; Mesitylene ; NMR ; Nuclear magnetic resonance ; Single crystals ; Solid state ; Spectrum analysis ; Synthesis ; Thermogravimetric analysis ; Washing ; Zinc ; Zinc compounds</subject><ispartof>New journal of chemistry, 2020, Vol.44 (1), p.129-14</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-63e7b93c49ca90972c0631adf1ba1dd98ee3347f4b5e71909a2914a39657196a3</citedby><cites>FETCH-LOGICAL-c281t-63e7b93c49ca90972c0631adf1ba1dd98ee3347f4b5e71909a2914a39657196a3</cites><orcidid>0000-0003-1772-135X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4009,27902,27903,27904</link.rule.ids></links><search><creatorcontrib>Vaddamanu, Moulali</creatorcontrib><creatorcontrib>Velappan, Kavitha</creatorcontrib><creatorcontrib>Prabusankar, Ganesan</creatorcontrib><title>Highly active mesoionic chalcogenone zinc() derivatives for C-S cross-coupling reactions</title><title>New journal of chemistry</title><description>The first mesoionic heavier chalcogenones,
L
1
-L
3
[
L
1
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone;
L
2
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione;
L
3
= 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(
ii
) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(
ii
) chalcogenone complexes, [(
L
1
)Zn(Cl)
2
(HOMe)] (
1
), [(
L
2
)Zn(Cl)
2
(HOMe)] (
3
) and [(
L
2
)Zn(Br)
2
(HOMe)] (
4
), and two dinuclear zinc complexes, [(
L
1
)Zn(Br)(μ
2
-Br)]
2
(
2
) and [(
L
3
)Zn(Br)(μ
2
-Br)]
2
(
5
), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes
1-5
represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(
ii
) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.
Mesoionic heavier chalcogenone complexes of zinc(
ii
) have been isolated and utilized as catalysts in C-S cross coupling reactions between thiophenols and aryl halides under convenient reaction conditions.</description><subject>Aromatic compounds</subject><subject>Chemical reactions</subject><subject>Cross coupling</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Crystals</subject><subject>Density functional theory</subject><subject>Derivatives</subject><subject>Halides</subject><subject>Ligands</subject><subject>Mesitylene</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Single crystals</subject><subject>Solid state</subject><subject>Spectrum analysis</subject><subject>Synthesis</subject><subject>Thermogravimetric analysis</subject><subject>Washing</subject><subject>Zinc</subject><subject>Zinc compounds</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpF0MFLwzAUBvAgCs7pxbsQ8KJCNS_J0uUoRZ1j6EEFbyVL0y2lS2bSDeZfb7aJnvICP773-BA6B3ILhMk7LV1DOOekOUA9YEJmkgo4TDNwnpEBF8foJMaGEIBcQA99juxs3m6w0p1dG7ww0VvvrMZ6rlrtZ8Z5Z_C3dfrqGlcm2LXawohrH3CRvWEdfIyZ9qtla90MB7NN8i6eoqNatdGc_b599PH48F6Mssnr03NxP8k0HUKXCWbyqWSaS60kkTnVRDBQVQ1TBVUlh8YwxvOaTwcmhyQUlcAVk2KQvkKxPrrc5y6D_1qZ2JWNXwWXVpaUUSHpMKUmdbNXu3ODqctlsAsVNiWQcttcWciX8a65ccIXexyi_nP_zbIfdz1qVg</recordid><startdate>2020</startdate><enddate>2020</enddate><creator>Vaddamanu, Moulali</creator><creator>Velappan, Kavitha</creator><creator>Prabusankar, Ganesan</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0003-1772-135X</orcidid></search><sort><creationdate>2020</creationdate><title>Highly active mesoionic chalcogenone zinc() derivatives for C-S cross-coupling reactions</title><author>Vaddamanu, Moulali ; Velappan, Kavitha ; Prabusankar, Ganesan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-63e7b93c49ca90972c0631adf1ba1dd98ee3347f4b5e71909a2914a39657196a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>Chemical reactions</topic><topic>Cross coupling</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Crystals</topic><topic>Density functional theory</topic><topic>Derivatives</topic><topic>Halides</topic><topic>Ligands</topic><topic>Mesitylene</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Single crystals</topic><topic>Solid state</topic><topic>Spectrum analysis</topic><topic>Synthesis</topic><topic>Thermogravimetric analysis</topic><topic>Washing</topic><topic>Zinc</topic><topic>Zinc compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vaddamanu, Moulali</creatorcontrib><creatorcontrib>Velappan, Kavitha</creatorcontrib><creatorcontrib>Prabusankar, Ganesan</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vaddamanu, Moulali</au><au>Velappan, Kavitha</au><au>Prabusankar, Ganesan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly active mesoionic chalcogenone zinc() derivatives for C-S cross-coupling reactions</atitle><jtitle>New journal of chemistry</jtitle><date>2020</date><risdate>2020</risdate><volume>44</volume><issue>1</issue><spage>129</spage><epage>14</epage><pages>129-14</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>The first mesoionic heavier chalcogenones,
L
1
-L
3
[
L
1
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone;
L
2
= 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione;
L
3
= 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(
ii
) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(
ii
) chalcogenone complexes, [(
L
1
)Zn(Cl)
2
(HOMe)] (
1
), [(
L
2
)Zn(Cl)
2
(HOMe)] (
3
) and [(
L
2
)Zn(Br)
2
(HOMe)] (
4
), and two dinuclear zinc complexes, [(
L
1
)Zn(Br)(μ
2
-Br)]
2
(
2
) and [(
L
3
)Zn(Br)(μ
2
-Br)]
2
(
5
), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes
1-5
represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(
ii
) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.
Mesoionic heavier chalcogenone complexes of zinc(
ii
) have been isolated and utilized as catalysts in C-S cross coupling reactions between thiophenols and aryl halides under convenient reaction conditions.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c9nj04440j</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0003-1772-135X</orcidid></addata></record> |
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language | eng |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Aromatic compounds Chemical reactions Cross coupling Crystal structure Crystallography Crystals Density functional theory Derivatives Halides Ligands Mesitylene NMR Nuclear magnetic resonance Single crystals Solid state Spectrum analysis Synthesis Thermogravimetric analysis Washing Zinc Zinc compounds |
title | Highly active mesoionic chalcogenone zinc() derivatives for C-S cross-coupling reactions |
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