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Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C-H Activation and Orthogonal Reactivity
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC. Uppsala Univ, Dept Chem BMC, S-75123 Uppsala, Sweden..
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England..
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2015 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 40, 11765-11769 p.Article in journal (Refereed) Published
Abstract [en]

(Pinacolato)boryl ortho-silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented postfunctionalization of fluoride-activated (hetero)aryne precursors, for example, as substrates in transition-metal catalysis, and offers valuable new possibilities for aryl boronate postfunctionalization without the use of specialized protecting groups.

Place, publisher, year, edition, pages
2015. Vol. 54, no 40, 11765-11769 p.
Keyword [en]
arynes, boron, C-H activation, chemoselectivity, synthetic methods
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-267329DOI: 10.1002/anie.201503152ISI: 000363394800029PubMedID: 26270451OAI: oai:DiVA.org:uu-267329DiVA: diva2:873645
Funder
Swedish Research CouncilCarl Tryggers foundation
Available from: 2015-11-24 Created: 2015-11-20 Last updated: 2017-12-01Bibliographically approved

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Devaraj, KarthikOrthaber, AndreasPilarski, Lukasz T.

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