Abstract
Although diaryl tellurides are parent organotellurium compounds, their synthesis methods, especially for unsymmetrical ones, are limited. This may be due to the instability of diaryl tellurides and their synthesis intermediates under reaction conditions. Radical reactions are known to exhibit excellent functional group selectivity; therefore, we focused on a bimolecular homolytic substitution (SH2) reaction between the aryl radical and diaryl ditelluride. Aryl radicals are generated from arylhydrazines in air and captured by diaryl ditellurides, resulting in a selective formation of unsymmetrical diaryl tellurides with high yields. The electronic effects of the substituents on both arylhydrazines and diaryl ditellurides on the SH2 reaction of tellurium are also discussed in detail.
Highlights
Chen, Q.; Kodama, S.; Nomoto, A.; In heteroatom chemistry, the formation of carbon–heteroatom bonds is an important fundamental reaction, and a series of transition-metal-catalyzed coupling reactions between aryl compounds and heteroatoms have been widely used for the construction of carbon–heteroatom bonds [1,2,3,4]
We focused on bimolecular homolytic substitution (SH 2) reactions between aryl radicals and interelement compounds bearing a heteroatom–heteroatom single bond
The concept was as follows: (1) aryl radicals were generated from arylhydrazines or triarylbismuthines using air and/or sunlight; (2) aryl radicals were smoothly captured by interelement compounds based on the characteristic features of individual heteroatom–heteroatom single bonds; and (3) the high tolerance of the radical reaction to various functional groups and solvents was advantageously utilized in developing a versatile method for forming carbon–heteroatom bonds
Summary
Q.; Kodama, S.; Nomoto, A.; In heteroatom chemistry, the formation of carbon–heteroatom bonds is an important fundamental reaction, and a series of transition-metal-catalyzed coupling reactions between aryl compounds and heteroatoms have been widely used for the construction of carbon–heteroatom bonds [1,2,3,4]. The development of metal-free methods for carbon–heteroatom bond formation is strongly desired. To design such methods, we focused on bimolecular homolytic substitution (SH 2) reactions between aryl radicals and interelement compounds bearing a heteroatom–heteroatom single bond. The concept was as follows: (1) aryl radicals were generated from arylhydrazines or triarylbismuthines using air and/or sunlight; (2) aryl radicals were smoothly captured by interelement compounds based on the characteristic features of individual heteroatom–heteroatom single bonds; and (3) the high tolerance of the radical reaction to various functional groups and solvents was advantageously utilized in developing a versatile method for forming carbon–heteroatom bonds. Aryl radicals generated in air by the oxidation of arylhydrazine hydrochlorides or photoirradiation of triarylbismuthines were successfully trapped with
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