Metal-free sp³C–H functionalization: a novel approach for the syntheses of selenide ethers and thioesters from methyl arenes

Metal‐Catalyzed Synthesis and Use of Thioesters: Recent Developments

“…It was suggested and confirmed by competition experiments that the methyl group is first oxidized to an aldehyde. Interestingly, no metal catalyst was needed in the work of Lee et al., who just used disulfides and an oxidant . They proposed the initial formation of an thioether and its subsequent oxidation.…”

“…Interestingly,n om etal catalystw as neededi nt he work of Lee et al,w ho just used disulfides and an oxidant. [45] They proposed the initial formation of an thio-Scheme12. Copper-catalyzed coupling of aryl iodides with thiobenzoate.…”

Cross‐Dehydrogenative‐Coupling of Alkoxybenzenes with Toluenes: Copper(II) Halide Mediated Tandem Halo/Benzylation of Arenes

“…If the reaction was run under the standard conditions for twenty hours, then an additional one equivalent of copper(I) bromide added to the reaction vessel, followed by further heating for 24 further hours, then 43% of the expected product 4a was isolated along with a considerable quantity of di-xylylated product 10 (25%). Fourth, it is well known that the generation of radicals is possible from DTBH and benzylic C-H groups and heating; 24 with this in mind, the role of these radicals was assessed. When carrying out the benchmark reaction in the presence of 2.0 equivalents of radical trapping agents TEMPO and galvinoxyl radical, no diphenylmethane product 4a was observed (Figure 3g; only halogenated starting materials were detected).…”

“…Fourth, it is well knownt hat the generation of radicals is possible from DTBH and benzylic CÀHg roups and heating; [24] with this in mind, the role of these radicals was assessed. When carrying out the benchmark reactioni nt he presence of 2.0 equivalents of radicalt rappinga gents, TEMPOa nd galvinoxyl radical, no diphenylmethane product 4a was observed ( Figure 3g;only halogenated startingmaterials were detected).…”

Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C–N Bond Activation

“…14 When TEMPO was added to the cross-coupling of pyridinium 3a , known TEMPO adduct 27 was produced in 32% yield (Scheme 5). 17 Cross-coupled product 5 was not observed.…”