RESUMO
Correction for 'Regioselective O-alkylation of 2-pyridones by TfOH-catalyzed carbenoid insertion' by Zhewei Yan et al., Chem. Commun., 2023, 59, 106-109, https://doi.org/10.1039/d2cc05676c.
RESUMO
Selective alkylation of 2-pyridone could solve a challenge in chemistry and streamline the synthesis of important molecules. Here we report the regioselective O-alkylation of 2-pyridones by TfOH-catalyzed carbenoid insertion. In the catalytic system, alkylation of 2-pyridone was achieved with unprecedented regioselectiviy (>99 : 1). This protocol is characterized by mild reaction conditions, metal-free, and simplicity. Moreover, this method provides the desired products in good yield and demonstrates a broad substrate scope in this transformation.
Assuntos
Piridonas , Piridonas/química , Alquilação , CatáliseRESUMO
Selective alkylation of indazoles is still a highly challenging topic in chemistry and the synthesis of important molecules. Herein, a novel highly selective N2-alkylation of indazoles with diazo compounds is described in the presence of TfOH. Unlike the traditional metal- and base-catalysed version, this protocol highlights the regioselectivity of alkylation of indazoles and a metal-free catalysis system, affording N2-alkylated products in good to excellent yields with high regioselectivity (N2/N1 up to 100/0) and excellent functional group tolerance. Furthermore, a gram scale synthesis was conducted successfully to give rise to the corresponding products. Mechanistic studies through control experiments provide plausible mechanistic proposals.