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Abstract
A Rh(II)-catalyzed highly selective N2-arylation of benzotriazole is developed with wide scope and good functional group tolerance. The reaction is also extended on indazole and substituted 1,2,3-triazole scaffolds. In addition, late-stage arylation of benzotriazoles tethered with bioactive molecules is realized under the developed conditions. Control experiments and DFT calculations reveal that presumably, the reaction proceeds via nucleophilic addition of N2 (of 1H tautomer) center to metal-carbene followed by 1,5-H shift. This differs from classical X-H insertion into carbene centers and subsequent 1,2-H shift.
Supplementary materials
Title
Rh(II)-Catalysed N2-Selective Arylation of Benzotriazoles and Indazoles using Quinoid Carbenes via 1,5-H Shift
Description
A Rh(II)-catalyzed highly selective N2-arylation of benzotriazole is developed with wide scope and good functional group tolerance. The reaction is also extended on indazole and substituted 1,2,3-triazole scaffolds. In addition, late-stage arylation of benzotriazoles tethered with bioactive molecules is realized under the developed conditions. Control experiments and DFT calculations reveal that presumably, the reaction proceeds via nucleophilic addition of N2 (of 1H tautomer) center to metal-carbene followed by 1,5-H shift. This differs from classical X-H insertion into carbene centers and subsequent 1,2-H shift.
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