Oxidizing liquid media for chemical transformations

An oxidizing composition comprising:

• (a) an oxidizing electrophile comprising a main group element in oxidized form and at least one conjugate anion of an oxygen acid;
• (b) a non-oxidizable liquid selected from a fluorinated hydrocarbon, a sulfone, a deactivated arene, a deactivated aliphatic, a deactivated heteroarene, a deactivated heteroaliphatic, compound (I), and a combination thereof;
• wherein
• the deactivated arene and deactivated heteroarene comprise at least one electron withdrawing group selected from the group consisting of —NO2, fluoro-C1-8 alkyl, —F, —OOCR, —COOH, —OH2+, —CONH2, —COOR, —NR3+, —CN, —SO3H, —SO3R, —SO3W, and a combination thereof,
• the deactivated aliphatic and deactivated heteroaliphatic comprise at least one electron withdrawing group selected from the group consisting of —NO2, —CONH2, —NR3+, —CN, —SO3H, —SO3R, —SO3W, and a combination thereof, provided that the deactivated aliphatic and deactivated heteroaliphatic are not methanesulfonic acid,
• R is hydrogen or any aliphatic, heteroaliphatic, aromatic, or heteroaromatic moiety, each of which is optionally substituted with halo, hydroxyl, cyano, nitro, alkoxy, amino, aryl, heteroaryl, alkyl, heteroalkyl, oxo, or a combination thereof, and W is a cation comprising a metal selected from boron, bismuth, antimony, arsenic, lanthanum, cerium, scandium, yttrium, titanium, zirconium, hafnium, silver, zinc, cadmium, aluminum, gallium, indium, germanium, tin, phosphorus, an alkali metal, and an alkaline earth metal, and
• compound (I) is selected from trifluoromethanol, trifluoromethyl 2,2,2-trifluoroacetate, 2,2,2-trifluoroethan-1-ol, 2,2,2-trifluoroethyl 2,2,2-trifluoroacetate, perfluoroethyl 2,2,2-trifluoroacetate, 1,1,2,2,2-pentafluoroethan-1-ol, trifluoro(nitro)methane, 1,1,2,2-tetrafluoroethane-1,2-diol, 1,1,2,2-tetrafluoro-2-hydroxyethyl 2,2,2-trifluoroacetate, perfluoroethane-1,2-diyl bis(2,2,2-trifluoroacetate), 1,1,2,2,3,3-hexafluoropropane-1,3-diol, propane-1,2,3-triyl tris(2,2,2-trifluoroacetate), oxalic acid, 1,1,1,4,4,4-hexafluorobutane-2,3-dione, methyl 2,2,3,3,3-pentafluoropropanoate, trifluoromethyl 2,2,3,3,3-pentafluoropropanoate, trifluoromethyl acetate, 1,1-difluoroethyl acetate, 2,2,2-trifluoroethyl acetate, perfluoroethyl acetate, perfluoropropan-2-yl acetate, 1,1,1,3,3,3-hexafluoropropan-2-yl acetate, 1,1,2,2-tetrafluoro-2-hydroxyethyl acetate, perfluoroethane-1,2-diyl diacetate, ethane-1,2-diyl diacetate, propane-1,2,3-triyl trisacetate, perfluoropropane-1,2,3-triyl triacetate, 1,1,3,3-tetrafluoropropane-1,2,3-triyl triacetate, 1,1-difluoroethane-1,2-diyl diacetate, trifluoro(trifluoromethoxy)methane, 1,1,1,2,2-pentafluoro-2-(trifluoromethoxy)ethane, 1,1,1,2,2-pentafluoro-2-(perfluoroethoxy)ethane, tris(trifluoromethyl)amine, 1,1,2,2,2-pentafluoro-N-(perfluoroethyl)-N-(trifluoromethyl)ethan-1-amine, tris(perfluoroethyl)amine, 2,2,2-trifluoro-N,N-bis(trifluoromethyl)acetamide, NN-bis(trifluoromethyl)formamide, 2,2,2-trifluoroacetamide, perfluoropyrrolidine, perfluoropyrroline, perfluoropyran, perfluoropiperidine, perfluorodioxane, perfluoromorpholine, perfluoropiperazine, pyrrolidine carboxylic acid, pyrroline carboxylic acid, pyran carboxylic acid, piperidine carboxylic acid, dioxane carboxylic acid, morpholine carboxylic acid, piperazine carboxylic acid, and a combination thereof, and
• (c) optionally one or more salt additives of formula QaZb, wherein Q is a cation, Z is a bridging oxide, a terminal oxide, a hydroxide, or a conjugate anion of an oxygen acid, a is an integer from 1 to 5, and b is an integer from 1 to 5, wherein a and b are the same or different and balance the oxidation states of Q and Z;
• and
• wherein the non-oxidizable liquid is substantially inert in the presence of the oxidizing electrophile.