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Studying Regioisomer Formation in the Pd-Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification

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Title
Studying Regioisomer Formation in the Pd-Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification
Author(s)
Ye, Yuxuan; Seoung-Tae Kim; King, Ryan P.; Mu-Hyun Baik; Buchwald, Stephen L.
Publication Date
2023-04
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.62, no.15
Publisher
WILEY-V C H VERLAG GMBH
Abstract
Pd-catalyzed nucleophilic fluorination reactions are important methods for the synthesis of fluoroarenes and fluoroalkenes. However, these reactions can generate a mixture of regioisomeric products that are often difficult to separate. While investigating the Pd-catalyzed fluorination of cyclic vinyl triflates, we observed that the addition of a substoichiometric quantity of TESCF3 significantly improved the regioselectivity of the reaction. Herein, we report a combined experimental and computational study on the mechanism of this transformation focusing on the role of TESCF3. The poor regioselectivity of the reaction in the absence of additives results from the formation of LPd-cyclohexyne complexes (L=biaryl monophosphine ligand). When TESCF3 is added to the reaction mixture, the generation of the Pd-cyclohexyne complexes is diminished by an unexpected pathway involving the dearomatization of the ligand by nucleophilic attack from a trifluoromethyl anion (CF3-). © 2023The Authors.AngewandteChemieInternationalEditionpublishedby Wiley-VCHGmbH
URI
https://pr.ibs.re.kr/handle/8788114/13387
DOI
10.1002/anie.202300109
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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