Abstract:The 5-heterofunctionalized triazoles are important scaffolds in bioactive compounds,b ut current click reactions (CuAAC) cannot produce these core structures.Acopper(I)catalyzedi nterrupted click reaction to access diverse 5functionalizedt riazoles is reported. Various 5-amino-, thio-, and selenotriazoles were readily assembled in one step in high yields.T he reaction proceeds under mild conditions with complete regioselectivity.I ta lso features ab road substrate scope and good functional group compatibility.… Show more
“…Thus, Ruijter and co-workers reported a copper-catalyzed three-component synthesis of isothioureas from isocyanides, benzenesulfonothioates, and amines 43 . Xu and co-workers have also reported a copper-catalyzed C sp 2 –S bond formation for the synthesis of 5-thiotriazoles 44 . Fig.…”
Chalcogen-containing compounds have received considerable attention because of their manifold applications in agrochemicals, pharmaceuticals, and material science. While many classical methods have been developed for preparing organic sulfides, most of them exploited the transition-metal-catalyzed cross-couplings of aryl halides or pseudo halides with thiols or disulfides, with harsh reaction conditions usually being required. Herein, we present a user-friendly, nickel-catalyzed reductive thiolation of unactivated primary and secondary alkyl bromides with thiosulfonates as reliable thiolation reagents, which are easily prepared and bench-stable. Furthermore, a series of selenides is also prepared in a similar fashion with selenosulfonates as selenolation reagents. This catalytic method offers a facile synthesis of a wide range of unsymmetrical alkyl-aryl or alkyl-alkyl sulfides and selenides under mild conditions with an excellent tolerance of functional groups. Likewise, the use of sensitive and stoichiometric organometallic reagents can be avoided.
“…Thus, Ruijter and co-workers reported a copper-catalyzed three-component synthesis of isothioureas from isocyanides, benzenesulfonothioates, and amines 43 . Xu and co-workers have also reported a copper-catalyzed C sp 2 –S bond formation for the synthesis of 5-thiotriazoles 44 . Fig.…”
Chalcogen-containing compounds have received considerable attention because of their manifold applications in agrochemicals, pharmaceuticals, and material science. While many classical methods have been developed for preparing organic sulfides, most of them exploited the transition-metal-catalyzed cross-couplings of aryl halides or pseudo halides with thiols or disulfides, with harsh reaction conditions usually being required. Herein, we present a user-friendly, nickel-catalyzed reductive thiolation of unactivated primary and secondary alkyl bromides with thiosulfonates as reliable thiolation reagents, which are easily prepared and bench-stable. Furthermore, a series of selenides is also prepared in a similar fashion with selenosulfonates as selenolation reagents. This catalytic method offers a facile synthesis of a wide range of unsymmetrical alkyl-aryl or alkyl-alkyl sulfides and selenides under mild conditions with an excellent tolerance of functional groups. Likewise, the use of sensitive and stoichiometric organometallic reagents can be avoided.
“…Based on the above experiment results and related literatures, we proposed a plausible reaction mechanism for this Cu(I)‐catalyzed reaction (Scheme ). First, the intermediate A or its tautomer A′ is generated by the reaction of methyl 2‐isocyanoacetate 2 a and Cu 2 O.…”
A Copper-catalyzed reaction of aryl isocyanides with active methylene isocyanides and arylsulfonothioates is developed for the synthesis of sulfur-containing trisubstituted imidazoles. This reaction not only forms new CÀ C, CÀ N, and CÀ S bonds in one step, but also provides a new strategy for the construction of trisubstituted imidazoles based on the isocyanide-isocyanide [3 + 2] cycloaddition.
“…[10] Since Xu's group reported a Cu-catalyzed interrupted click reaction of terminal alkynes, azides and heteroatom electrophiles (PhSO 2 XR, X = S, Se) for constructing 5-thio-and selenotriazoles, such cascade strategy has become a powerful tool for synthesis of 5-chalcogenotriazoles. [11] Cu-catalyzed decarboxylation/cyclization of alkynyl carboxylic acids was developed by Pan and Xu to achieve 5-selenotriazoles using diselenides as selenium source. [12] Wu and co-workers also reported stoichiometric Cu-mediated multicomponent reaction for the synthesis of 5chalcogenotriazoles from terminal alkynes, azides, coupling partners (organohalides, tosylates, boronic acids and TMSCF 3 ) and Se/S 8 .…”
A copper-catalyzed four-component cascade reaction for the preparation of triazoles bearing β-hydroxy chalcogenides from terminal alkynes, azides, epoxides, and Se/K 2 S is reported. The present reaction proceeds under mild conditions, and exhibits a good functional group compatibility. A possible mechanism is proposed.
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