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Catalyst-Free Trifluoromethoxylation of Silyl Enol Ethers and Allyl Silanes with Bis(trifluoromethyl)peroxide

Lookup NU author(s): Dr Matt HopkinsonORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

Radical trifluoromethoxylation is an attractive approach to prepare compounds featuring the important OCF₃ group, however most existing methods have focused on aromatic substrates. Here, we report novel methodologies with alkenyl substrates employing bis(trifluoromethyl)peroxide (BTMP) as a practical and comparatively atom economical trifluoromethoxylating reagent. With silyl enol ether substrates, switching reaction solvent allows for the synthesis of either α-(trifluoromethoxy)ketone products or unprecedented alkenyl-OCF₃ species. Furthermore, allyl silanes have been employed as substrates for the first time, affording allyl(trifluoromethyl)ether products in good yields. In each case, the methods operate at room temperature without large excesses of the alkene substrate while, in contrast to previous radical trifluoromethoxylation reactions, no catalyst, light or other activators are required.

Publication metadata

Author(s): Maas LM, Fasting C, Voßnacker P, Limberg N, Golz P, Müller C, Riedel S, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Angewandte Chemie International Edition

Year: 2024

Volume: 63

Issue: 7

Print publication date: 12/02/2024

Online publication date: 22/12/2023

Acceptance date: 21/12/2023

Date deposited: 03/01/2024

ISSN (print): 1433-7851

ISSN (electronic): 1521-3773

Publisher: Wiley-VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/anie.202317770

DOI: 10.1002/anie.202317770

Data Access Statement: The data that support the findings of this study are available from the corresponding author upon reasonable request.

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