A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.
Herein, we report a method that provides an array of benzocyclobutanol and benzocyclobutylamine derivatives with broad substrate scope and good functional group tolerance under mild reaction conditions. The reaction proceeds by engaging triplet biradical atom transfer of olefinic compounds in the activation of remote C(sp 3 )À H bonds upon visible-light irradiation. The reaction mechanism involves the generation of triplet excited state of diarylethylene derivative and subsequent HAT process, and then the further ringclosing reaction affording the product via an electrocyclization process. The plausible mechanism is supported by control and deuterium labeling experiments, kinetic analysis, and DFT calculations.
A Cu(I)-catalyzed [3 + 2] intramolecular cycloaddition reaction of N-indole-tethered cyclopropenes is presented in this paper. This reaction starts from the formation of π-allyl cationic intermediate or its resonance-stabilized metal carbenoid intermediate upon activation of cyclopropene with Cu(I) catalyst and a Friedel−Crafts-type cyclization to give functionalized hydrogenated diazabenzo[a]cyclopenta[cd]azulenes in good to excellent yields along with moderate to good dr values. The asymmetric variant of this cycloaddition reaction can be realized, giving the desired products with moderate ee values.
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