Loading…

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-...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2023-04, Vol.47 (14), p.6871-6879
Main Authors: Gahlaut, Puneet Singh, Gautam, Deepak, Lama, Prem, Jana, Barun
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c281t-b19ad298431a5327cc02126fb950eb2bb734eb837d159457c57ce4b8871ff73c3
cites cdi_FETCH-LOGICAL-c281t-b19ad298431a5327cc02126fb950eb2bb734eb837d159457c57ce4b8871ff73c3
container_end_page 6879
container_issue 14
container_start_page 6871
container_title New journal of chemistry
container_volume 47
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
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2794517730</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2794517730</sourcerecordid><originalsourceid>FETCH-LOGICAL-c281t-b19ad298431a5327cc02126fb950eb2bb734eb837d159457c57ce4b8871ff73c3</originalsourceid><addsrcrecordid>eNpF0d1LwzAQAPAiCs7pi-9CwBeVRXNJ27S-yfxmfoDuuaRpOjO7pqYN2D35p5s5UTi4g_zuAndBsA_kFAhLzwpWzwmhJJYbwQBYnOKUxrDpawhDTKIw3g522tYbAB7DIPia1q51okLSGFvoWnTa1MiUSCAY0RHDndViaaq-wk1vtRcKVXom6gLp2qPn4ujY9y6aSn2eI9E0lZbrGf65e1PoxS3du8YPuhfOCk-dJ_UMWSXkyu0GW6WoWrX3m4fB9PrqdXyLJ083d-OLCZY0gQ7nkIqCpknIQESMcikJBRqXeRoRldM85yxUecJ4AVEaRlz6UGGeJBzKkjPJhsHhem5jzYdTbZfNjbO1_zKj3HcA54x4dbJW0pq2tarMGqsXwvYZkGy14eySPd7_bHjs8cEa21b-uf8LsG_KYngB</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2794517730</pqid></control><display><type>article</type><title>Unusual coordination of a 1,2,3-triazolyl-pyridine ligand in a Pd() complex: application in the Suzuki-Miyaura coupling reaction</title><source>Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)</source><creator>Gahlaut, Puneet Singh ; Gautam, Deepak ; Lama, Prem ; Jana, Barun</creator><creatorcontrib>Gahlaut, Puneet Singh ; Gautam, Deepak ; Lama, Prem ; Jana, Barun</creatorcontrib><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><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>
fulltext fulltext
identifier ISSN: 1144-0546
ispartof New journal of chemistry, 2023-04, Vol.47 (14), p.6871-6879
issn 1144-0546
1369-9261
language eng
recordid cdi_proquest_journals_2794517730
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
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-09T08%3A07%3A11IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Unusual%20coordination%20of%20a%201,2,3-triazolyl-pyridine%20ligand%20in%20a%20Pd()%20complex:%20application%20in%20the%20Suzuki-Miyaura%20coupling%20reaction&rft.jtitle=New%20journal%20of%20chemistry&rft.au=Gahlaut,%20Puneet%20Singh&rft.date=2023-04-03&rft.volume=47&rft.issue=14&rft.spage=6871&rft.epage=6879&rft.pages=6871-6879&rft.issn=1144-0546&rft.eissn=1369-9261&rft_id=info:doi/10.1039/d3nj00206c&rft_dat=%3Cproquest_cross%3E2794517730%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c281t-b19ad298431a5327cc02126fb950eb2bb734eb837d159457c57ce4b8871ff73c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2794517730&rft_id=info:pmid/&rfr_iscdi=true