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Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England.ORCID iD: 0000-0001-8619-7745
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2019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 9, p. 5863-5871Article in journal (Refereed) Published
Abstract [en]

A new, operationally simple approach is presented to access arynes and their fluoride-activated precursors based on Ru-catalyzed C-H silylation of arylboronates. Chromatographic purification may be deferred until after aryne capture, rendering the arylboronates de facto precursors. Access to various new arynes and their derivatives is demonstrated, including, for the first time, those based on a 2,3-carbazolyne and 2,3-fluorenyne core, which pave the way for novel derivatizations of motifs relevant to materials chemistry.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2019. Vol. 84, no 9, p. 5863-5871
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Organic Chemistry
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URN: urn:nbn:se:uu:diva-387960DOI: 10.1021/acs.joc.9b00221ISI: 000467319600089PubMedID: 30835118OAI: oai:DiVA.org:uu-387960DiVA, id: diva2:1332026
Funder
Swedish Research CouncilCarl Tryggers foundation Available from: 2019-06-27 Created: 2019-06-27 Last updated: 2019-06-27Bibliographically approved

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Devaraj, KarthikIngner, FredricSollert, CarinaOrthaber, AndreasPilarski, Lukasz T.

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