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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 \u03b1\u2010(trifluoromethoxy)ketone products or unprecedented alkenyl\u2010OCF<jats:sub>3<\/jats:sub> 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.<\/jats:p>","DOI":"10.1002\/anie.202317770","type":"journal-article","created":{"date-parts":[[2023,12,22]],"date-time":"2023-12-22T12:19:15Z","timestamp":1703247555000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Catalyst\u2010Free Trifluoromethoxylation of Silyl Enol Ethers and Allyl Silanes with Bis(trifluoromethyl)peroxide"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1399-947X","authenticated-orcid":false,"given":"Lilian M.","family":"Maas","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Chemie und Biochemie\u2014Anorganische Chemie Freie Universit\u00e4t Berlin  Fabeckstra\u00dfe 34\/36 14195 Berlin Germany"},{"name":"School of 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N.Hopkinson S.Dix P.Golz J. R.Schmid H.Pernice S.Gutmann (Solvay) WO2022175508 2022."},{"key":"e_1_2_8_82_1","doi-asserted-by":"publisher","DOI":"10.1002\/j.0037-9646.1933.tb00009.x"},{"key":"e_1_2_8_83_1","unstructured":"\u00a0"},{"key":"e_1_2_8_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01578a013"},{"key":"e_1_2_8_85_2","unstructured":"G.\u2005H. Dreyhsig Master's Thesis Freie Universit\u00e4t Berlin (Germany)2022;"},{"key":"e_1_2_8_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp994434w"},{"key":"e_1_2_8_87_1","unstructured":"\u00a0"},{"key":"e_1_2_8_88_2","unstructured":"R. S.Porter G. H.Cady US3230264\u2005A 1966;"},{"key":"e_1_2_8_89_2","unstructured":"R. G.Syvret B. A.Allentown G. A.Cooper (Inc. 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Similar hyperconjugative interactions are thought to lay behind the unconventional conformational preferences observed with (trifluoromethoxy)arenes (see ref.\u2005[1])."},{"key":"e_1_2_8_104_1","unstructured":"Deposition numbers2306068 (for2\u2009k) 2306494 (for (Z)-4\u2009r)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_8_105_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0028-1088155"},{"key":"e_1_2_8_106_1","unstructured":"DFT calculations on (Z)- and (E)-4\u2009arevealed there is little difference in the thermodynamic stability of the isomers with (Z)-4\u2009abeing only 0.1\u2005kJ\/mol more stable than (E)-4\u2009ain DCM at 298.15\u2005K which is within the systematic error of the method. This implies the moderate diastereoselectivity observed results from kinetic factors during the deprotonation step."},{"key":"e_1_2_8_107_1","unstructured":"Surprisingly treatment of (Z)-4\u2009awith tetra-n-butylammonium fluoride (TBAF 1.2\u2005equiv.) in DCM at rt led to decomposition although desilylation reactivity was somewhat recovered employing potassium fluoride (19F NMR yield of2\u2009a=16\u2009% after 16\u2005h at 70\u2009\u00b0C)."},{"key":"e_1_2_8_108_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol403709g"},{"key":"e_1_2_8_109_1","unstructured":"Cyclic voltammetry measurements of BTMP and silyl enol ether3\u2009arevealed reduction and oxidation peaks respectively. The irreversibility of these redox events and the instability of the decomposition products however make it difficult to give a definitive statement about the reduction potentials especially for BTMP."},{"key":"e_1_2_8_110_1","unstructured":"Alternative potential reaction pathways include direct nucleophilic attack of the silyl enol ether onto BTMP generating cationEdirectly or a formal [2+2]-cycloaddition generating the 1 2-di(trifluoromethoxy)alkene intermediateF(Scheme\u2005)."},{"key":"e_1_2_8_111_1","unstructured":"In the presence of TEMPO direct single electron transfer between the catalyst and BTMP could occur providing an \u22c5OCF3radical without concomitant formation of a reactive radical cation intermediate. In this case radical addition to the silyl enol ether or potentially benzene starting materials as part of a radical chain seemingly occurs."},{"key":"e_1_2_8_112_1","unstructured":"The origin of the solvent-dependent switch in product distribution is not abundantly clear; however the different solubility of the KF generated as a reaction side-product could play a role. The generation of a strong Si\u2212F bond is likely a driving force behind the desilylation process and it could be expected that a higher effective fluoride concentration would favor the formation of ketones2. A test reaction conducted with CaCO3in place of K2CO3was accordingly performed to test this hypothesis. In this reaction the CaF2formed as side-product is essentially insoluble and even in more polar solvents the degree of desilylation would be expected to be lower. Indeed under the standard conditions with3\u2009ain acetone much less of the ketone2\u2009a(19F NMR yield=15\u2009%) was observed with OCF3-conatining alkene4\u2009abeing obtained as the major product (10\u2009:\u200932\u2009%). 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