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dc.contributor.authorZernickel, Anna
dc.contributor.authordu, weiyuan
dc.contributor.authorGhorpade, Seema
dc.contributor.authorSawant, Dinesh
dc.contributor.authorMakki, Arwa
dc.contributor.authorSekar, Nagaiyan
dc.contributor.authorEppinger, Jörg
dc.date.accessioned2018-01-15T06:10:39Z
dc.date.available2018-01-15T06:10:39Z
dc.date.issued2018-01-30
dc.identifier.citationZernickel A, Du W, Ghorpade S, Sawant DN, Makki AA, et al. (2018) Bedford-type palladacycle catalyzed Miyaura-borylation of aryl halides with tetrahydroxydiboron in water. The Journal of Organic Chemistry. Available: http://dx.doi.org/10.1021/acs.joc.7b02771.
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.doi10.1021/acs.joc.7b02771
dc.identifier.urihttp://hdl.handle.net/10754/626747
dc.description.abstractA mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 hours in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
dc.description.sponsorshipThis work was supported by the King Abdullah University of Science and Technology (KAUST baseline funding and GCR grant FIC/2010/07). Authors are gratefully acknowledging support from King Abdullah University of Science and Technology (KAUST), Saudi Arabia.
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttp://pubs.acs.org/doi/10.1021/acs.joc.7b02771
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/10.1021/acs.joc.7b02771.
dc.subjectMiyaura-borylation
dc.subjectPalladacycle
dc.subjectTetrahydroxydiboron
dc.subjectArylboronic acids
dc.titleBedford-type palladacycle catalyzed Miyaura-borylation of aryl halides with tetrahydroxydiboron in water
dc.typeArticle
dc.contributor.departmentBiological & Organometallic Catalysis Laboratories
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentChemical Engineering Program
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentKAUST Solar Center (KSC)
dc.contributor.departmentOffice of the VP
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.contributor.departmentYoung Talent Development
dc.identifier.journalThe Journal of Organic Chemistry
dc.eprint.versionPost-print
dc.contributor.institutionDepartment of Dyestuff Technology, Institute of Chemical Technology (Deemed University), N. Parekh Marg, Matunga, Mumbai-400019, Maharashtra, India
dc.contributor.institutionLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Straße 29a, 18059 Rostock, Germany
kaust.personZernickel, Anna
kaust.personDu, Weiyuan
kaust.personGhorpade, Seema
kaust.personSawant, Dinesh
kaust.personMakki, Arwa
kaust.personEppinger, Jorg
kaust.grant.numberFIC/2010/07
refterms.dateFOA2019-01-09T00:00:00Z
dc.date.published-online2018-01-30
dc.date.published-print2018-02-16


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