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Mechanisms of Rh-Catalyzed Oxyfluorination and Oxytrifluoromethylation of Diazocarbonyl Compounds with Hypervalent Fluoroiodine
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Rekke forfattare: 32018 (engelsk)Inngår i: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 8, nr 5, s. 4483-4492Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The reaction mechanisms of rhodium-catalyzed geminal oxyfluorination and oxytrifluoromethylation of diazo-carbonyl compounds with fluoro-benziodoxole and Togni reagents are investigated by means of density functional theory calculations. It is shown that the two reactions follow very similar mechanisms, involving N-2 dissociation to form a Rh-carbene intermediate, alcohol insertion and proton transfer resulting in a stable Rh-enol intermediate, and concerted proton transfer/electrophilic addition of the hypervalent iodine reagent to the enol. Isomerization of the hypervalent iodine takes then place before a ligand coupling affords the final product. The role of the dirhodium catalyst in facilitating the various steps of the reaction is discussed. The presented mechanisms are consistent with available experimental information, and the obtained insights allow for extension to other reactions involving hypervalent iodine reagents.

sted, utgiver, år, opplag, sider
2018. Vol. 8, nr 5, s. 4483-4492
Emneord [en]
fluorination, trifluoromethylation, hypervalent iodine, reaction mechanism, DFT calculations
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-158167DOI: 10.1021/acscatal.8b00667ISI: 000431727300083OAI: oai:DiVA.org:su-158167DiVA, id: diva2:1234204
Tilgjengelig fra: 2018-07-23 Laget: 2018-07-23 Sist oppdatert: 2019-01-03bibliografisk kontrollert

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