Synthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Ester

Handle URI:
http://hdl.handle.net/10754/622480
Title:
Synthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Ester
Authors:
Batool, Farhat; Emwas, Abdul-Hamid M.; Gao, Xin ( 0000-0002-7108-3574 ) ; Munawar, Munawar A.; Chotana, Ghayoor A.
Abstract:
Iridium-catalyzed aromatic borylation provides quick one-step access to 2,6-bis(trifluoromethyl)pyridine-4-boronic acid pinacol ester. Suzuki couplings of this highly electron-deficient pyridine-4-boronic ester with various (hetero)aryl bromides was successfully carried out and the coupled products were obtained in 46–95% isolated yields. Double and triple Suzuki couplings, with dibromo- and tribromoarenes, respectively, were also achieved. Thus demonstrating that this pyridine-4-boronic ester can be a useful source for the installation of one of the strongest electron-withdrawing aromatic group in organic compounds. Copyright © 2016, Georg Thieme Verlag. All rights reserved.
KAUST Department:
Imaging and Characterization Core Lab; Computational Bioscience Research Center (CBRC); Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division
Citation:
Chotana G, Batool F, Emwas A-H, Gao X, Munawar M (2016) Synthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Ester. Synthesis. Available: http://dx.doi.org/10.1055/s-0036-1588344.
Publisher:
Thieme Publishing Group
Journal:
Synthesis
Issue Date:
18-Nov-2016
DOI:
10.1055/s-0036-1588344
Type:
Article
ISSN:
0039-7881; 1437-210X
Sponsors:
We thank Lahore University of Management Sciences for providing generous financial support for this research through start-up grant and through faculty initiative fund to GAC. This work was partly supported by King Abdullah University of Science and Technology (KAUST), and by University of the Punjab, Lahore, Pakistan. We are thankful to SBA for financial support for the purchase of GC-MS. We are thankful to Ms. Noor-ul-Ann for her assistance in some part of the experimental work. We extend our acknowledgement to KAUST core labs facilities for NMR and HRMS measurements.
Additional Links:
https://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1588344
Appears in Collections:
Articles; Advanced Nanofabrication, Imaging and Characterization Core Lab; Computational Bioscience Research Center (CBRC); Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorBatool, Farhaten
dc.contributor.authorEmwas, Abdul-Hamid M.en
dc.contributor.authorGao, Xinen
dc.contributor.authorMunawar, Munawar A.en
dc.contributor.authorChotana, Ghayoor A.en
dc.date.accessioned2017-01-02T09:28:33Z-
dc.date.available2017-01-02T09:28:33Z-
dc.date.issued2016-11-18en
dc.identifier.citationChotana G, Batool F, Emwas A-H, Gao X, Munawar M (2016) Synthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Ester. Synthesis. Available: http://dx.doi.org/10.1055/s-0036-1588344.en
dc.identifier.issn0039-7881en
dc.identifier.issn1437-210Xen
dc.identifier.doi10.1055/s-0036-1588344en
dc.identifier.urihttp://hdl.handle.net/10754/622480-
dc.description.abstractIridium-catalyzed aromatic borylation provides quick one-step access to 2,6-bis(trifluoromethyl)pyridine-4-boronic acid pinacol ester. Suzuki couplings of this highly electron-deficient pyridine-4-boronic ester with various (hetero)aryl bromides was successfully carried out and the coupled products were obtained in 46–95% isolated yields. Double and triple Suzuki couplings, with dibromo- and tribromoarenes, respectively, were also achieved. Thus demonstrating that this pyridine-4-boronic ester can be a useful source for the installation of one of the strongest electron-withdrawing aromatic group in organic compounds. Copyright © 2016, Georg Thieme Verlag. All rights reserved.en
dc.description.sponsorshipWe thank Lahore University of Management Sciences for providing generous financial support for this research through start-up grant and through faculty initiative fund to GAC. This work was partly supported by King Abdullah University of Science and Technology (KAUST), and by University of the Punjab, Lahore, Pakistan. We are thankful to SBA for financial support for the purchase of GC-MS. We are thankful to Ms. Noor-ul-Ann for her assistance in some part of the experimental work. We extend our acknowledgement to KAUST core labs facilities for NMR and HRMS measurements.en
dc.publisherThieme Publishing Groupen
dc.relation.urlhttps://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1588344en
dc.subject2,6-bis(trifluoromethyl)pyridineen
dc.subjectboronic estersen
dc.subjectborylationen
dc.subjectC–H activationen
dc.subjectiridium catalysisen
dc.subjectorganic electronic materialsen
dc.subjectSuzuki couplingen
dc.titleSynthesis and Suzuki Cross-Coupling Reactions of 2,6-Bis(trifluoromethyl)pyridine-4-boronic Acid Pinacol Esteren
dc.typeArticleen
dc.contributor.departmentImaging and Characterization Core Laben
dc.contributor.departmentComputational Bioscience Research Center (CBRC)en
dc.contributor.departmentComputer, Electrical and Mathematical Sciences and Engineering (CEMSE) Divisionen
dc.identifier.journalSynthesisen
dc.contributor.institutionDepartment of Chemistry, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistanen
dc.contributor.institutionInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistanen
kaust.authorEmwas, Abdul-Hamid M.en
kaust.authorGao, Xinen
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