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Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd() complex: application in the Suzuki-Miyaura coupling reaction
A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] ( 2 ) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an ortho -phthalic acid platform [bptmp] ( 3 ). The [bptmp] ligand is prepared to produce transition metal complexes through selective N-...
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Published in: | New journal of chemistry 2023-04, Vol.47 (14), p.6871-6879 |
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creator | Gahlaut, Puneet Singh Gautam, Deepak Lama, Prem Jana, Barun |
description | A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] (
2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
). The [bptmp] ligand is prepared to produce transition metal complexes through selective N-3 coordination of the
inverse
triazolyl-pyridine ligand. An equimolar reaction between [bptmp] (
3
) and PdCl
2
(CH
3
CN)
2
in acetonitrile leads to the isolation of a light-yellow solid (
4
). Several spectroscopic and spectrometry data established that the formed complex has a molecular formula of PdCl
2
[bptmp] (
4
). Molecular structure determination using a single crystal X-ray diffraction study further established the formation of a 1 : 1 metal-ligand complex, where PdCl
2
bridges the two side-arms of the phthalic acid platform. As per the design of [bptmp], in complex (
4
), the chelating bidentate triazolyl-pyridine units are not coordinated, whereas the N-3 nitrogen of the
inverse
triazolyl-pyridine selectively coordinated to Pd(
ii
). Furthermore, complex (
4
) is proved to be a highly effective catalyst for the Suzuki-Miyaura coupling reaction in a water/ethanol solvent combination with very modest catalyst loading. The high reactivity of complex
4
in the catalytic Suzuki-Miyaura coupling reaction is attributed to the electronic and steric properties of the [bptmp] ligand.
A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] (
2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
). |
doi_str_mv | 10.1039/d3nj00206c |
format | article |
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2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
). The [bptmp] ligand is prepared to produce transition metal complexes through selective N-3 coordination of the
inverse
triazolyl-pyridine ligand. An equimolar reaction between [bptmp] (
3
) and PdCl
2
(CH
3
CN)
2
in acetonitrile leads to the isolation of a light-yellow solid (
4
). Several spectroscopic and spectrometry data established that the formed complex has a molecular formula of PdCl
2
[bptmp] (
4
). Molecular structure determination using a single crystal X-ray diffraction study further established the formation of a 1 : 1 metal-ligand complex, where PdCl
2
bridges the two side-arms of the phthalic acid platform. As per the design of [bptmp], in complex (
4
), the chelating bidentate triazolyl-pyridine units are not coordinated, whereas the N-3 nitrogen of the
inverse
triazolyl-pyridine selectively coordinated to Pd(
ii
). Furthermore, complex (
4
) is proved to be a highly effective catalyst for the Suzuki-Miyaura coupling reaction in a water/ethanol solvent combination with very modest catalyst loading. The high reactivity of complex
4
in the catalytic Suzuki-Miyaura coupling reaction is attributed to the electronic and steric properties of the [bptmp] ligand.
A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] (
2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
).</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d3nj00206c</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acetonitrile ; Catalysts ; Chelation ; Chemical reactions ; Coordination compounds ; Coupling (molecular) ; Ethanol ; Ligands ; Molecular structure ; Nitrogen ; Palladium ; Pyridines ; Single crystals ; Transition metal compounds</subject><ispartof>New journal of chemistry, 2023-04, Vol.47 (14), p.6871-6879</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-b19ad298431a5327cc02126fb950eb2bb734eb837d159457c57ce4b8871ff73c3</citedby><cites>FETCH-LOGICAL-c281t-b19ad298431a5327cc02126fb950eb2bb734eb837d159457c57ce4b8871ff73c3</cites><orcidid>0000-0003-0706-4712 ; 0000-0002-8055-7081</orcidid></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>Gahlaut, Puneet Singh</creatorcontrib><creatorcontrib>Gautam, Deepak</creatorcontrib><creatorcontrib>Lama, Prem</creatorcontrib><creatorcontrib>Jana, Barun</creatorcontrib><title>Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd() complex: application in the Suzuki-Miyaura coupling reaction</title><title>New journal of chemistry</title><description>A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] (
2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
). The [bptmp] ligand is prepared to produce transition metal complexes through selective N-3 coordination of the
inverse
triazolyl-pyridine ligand. An equimolar reaction between [bptmp] (
3
) and PdCl
2
(CH
3
CN)
2
in acetonitrile leads to the isolation of a light-yellow solid (
4
). Several spectroscopic and spectrometry data established that the formed complex has a molecular formula of PdCl
2
[bptmp] (
4
). Molecular structure determination using a single crystal X-ray diffraction study further established the formation of a 1 : 1 metal-ligand complex, where PdCl
2
bridges the two side-arms of the phthalic acid platform. As per the design of [bptmp], in complex (
4
), the chelating bidentate triazolyl-pyridine units are not coordinated, whereas the N-3 nitrogen of the
inverse
triazolyl-pyridine selectively coordinated to Pd(
ii
). Furthermore, complex (
4
) is proved to be a highly effective catalyst for the Suzuki-Miyaura coupling reaction in a water/ethanol solvent combination with very modest catalyst loading. The high reactivity of complex
4
in the catalytic Suzuki-Miyaura coupling reaction is attributed to the electronic and steric properties of the [bptmp] ligand.
A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] (
2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
).</description><subject>Acetonitrile</subject><subject>Catalysts</subject><subject>Chelation</subject><subject>Chemical reactions</subject><subject>Coordination compounds</subject><subject>Coupling (molecular)</subject><subject>Ethanol</subject><subject>Ligands</subject><subject>Molecular structure</subject><subject>Nitrogen</subject><subject>Palladium</subject><subject>Pyridines</subject><subject>Single crystals</subject><subject>Transition metal compounds</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpF0d1LwzAQAPAiCs7pi-9CwBeVRXNJ27S-yfxmfoDuuaRpOjO7pqYN2D35p5s5UTi4g_zuAndBsA_kFAhLzwpWzwmhJJYbwQBYnOKUxrDpawhDTKIw3g522tYbAB7DIPia1q51okLSGFvoWnTa1MiUSCAY0RHDndViaaq-wk1vtRcKVXom6gLp2qPn4ujY9y6aSn2eI9E0lZbrGf65e1PoxS3du8YPuhfOCk-dJ_UMWSXkyu0GW6WoWrX3m4fB9PrqdXyLJ083d-OLCZY0gQ7nkIqCpknIQESMcikJBRqXeRoRldM85yxUecJ4AVEaRlz6UGGeJBzKkjPJhsHhem5jzYdTbZfNjbO1_zKj3HcA54x4dbJW0pq2tarMGqsXwvYZkGy14eySPd7_bHjs8cEa21b-uf8LsG_KYngB</recordid><startdate>20230403</startdate><enddate>20230403</enddate><creator>Gahlaut, Puneet Singh</creator><creator>Gautam, Deepak</creator><creator>Lama, Prem</creator><creator>Jana, Barun</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/0000-0003-0706-4712</orcidid><orcidid>https://orcid.org/0000-0002-8055-7081</orcidid></search><sort><creationdate>20230403</creationdate><title>Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd() complex: application in the Suzuki-Miyaura coupling reaction</title><author>Gahlaut, Puneet Singh ; Gautam, Deepak ; Lama, Prem ; Jana, Barun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-b19ad298431a5327cc02126fb950eb2bb734eb837d159457c57ce4b8871ff73c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetonitrile</topic><topic>Catalysts</topic><topic>Chelation</topic><topic>Chemical reactions</topic><topic>Coordination compounds</topic><topic>Coupling (molecular)</topic><topic>Ethanol</topic><topic>Ligands</topic><topic>Molecular structure</topic><topic>Nitrogen</topic><topic>Palladium</topic><topic>Pyridines</topic><topic>Single crystals</topic><topic>Transition metal compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gahlaut, Puneet Singh</creatorcontrib><creatorcontrib>Gautam, Deepak</creatorcontrib><creatorcontrib>Lama, Prem</creatorcontrib><creatorcontrib>Jana, Barun</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>Gahlaut, Puneet Singh</au><au>Gautam, Deepak</au><au>Lama, Prem</au><au>Jana, Barun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd() complex: application in the Suzuki-Miyaura coupling reaction</atitle><jtitle>New journal of chemistry</jtitle><date>2023-04-03</date><risdate>2023</risdate><volume>47</volume><issue>14</issue><spage>6871</spage><epage>6879</epage><pages>6871-6879</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] (
2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
). The [bptmp] ligand is prepared to produce transition metal complexes through selective N-3 coordination of the
inverse
triazolyl-pyridine ligand. An equimolar reaction between [bptmp] (
3
) and PdCl
2
(CH
3
CN)
2
in acetonitrile leads to the isolation of a light-yellow solid (
4
). Several spectroscopic and spectrometry data established that the formed complex has a molecular formula of PdCl
2
[bptmp] (
4
). Molecular structure determination using a single crystal X-ray diffraction study further established the formation of a 1 : 1 metal-ligand complex, where PdCl
2
bridges the two side-arms of the phthalic acid platform. As per the design of [bptmp], in complex (
4
), the chelating bidentate triazolyl-pyridine units are not coordinated, whereas the N-3 nitrogen of the
inverse
triazolyl-pyridine selectively coordinated to Pd(
ii
). Furthermore, complex (
4
) is proved to be a highly effective catalyst for the Suzuki-Miyaura coupling reaction in a water/ethanol solvent combination with very modest catalyst loading. The high reactivity of complex
4
in the catalytic Suzuki-Miyaura coupling reaction is attributed to the electronic and steric properties of the [bptmp] ligand.
A modified "click" reaction between 2-azidopyridine and di(prop-2-yn-1-yl)phthalate [dpp] (
2
) produces a novel bis(1,2,3-triazolyl-pyridine) ligand on an
ortho
-phthalic acid platform [bptmp] (
3
).</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d3nj00206c</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-0706-4712</orcidid><orcidid>https://orcid.org/0000-0002-8055-7081</orcidid></addata></record> |
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language | eng |
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source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
subjects | Acetonitrile Catalysts Chelation Chemical reactions Coordination compounds Coupling (molecular) Ethanol Ligands Molecular structure Nitrogen Palladium Pyridines Single crystals Transition metal compounds |
title | Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd() complex: application in the Suzuki-Miyaura coupling reaction |
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