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

Author:

Maas Lilian M.12ORCID,Fasting Carlo1ORCID,Voßnacker Patrick1ORCID,Limberg Niklas1ORCID,Golz Paul1ORCID,Müller Carsten1ORCID,Riedel Sebastian1ORCID,Hopkinson Matthew N.12ORCID

Affiliation:

1. Institut für Chemie und Biochemie—Anorganische Chemie Freie Universität Berlin Fabeckstraße 34/36 14195 Berlin Germany

2. School of Natural and Environmental Sciences Newcastle University Bedson Building Newcastle upon Tyne NE1 7RU UK

Abstract

AbstractRadical 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.

Funder

Friedrich-Ebert-Stiftung

Dahlem Research School, Freie Universität Berlin

Daimler und Benz Stiftung

Deutsche Forschungsgemeinschaft

Verband der Chemischen Industrie

Publisher

Wiley

Subject

General Medicine

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