The first site-selective electrochemical alkylation of tropones is realized by reacting 2-acetoxytropones and redox-active-esters (RAEs). The electroreductive protocol enables the preparation of mono- and disubstituted tropones in high yields (up to 71%) under very mild conditions. Dedicated voltammetric measurements served for the identification of 2-acetoxytropones as a class of valuable trapping agents of nucleophilic radical species and shed light on the whole mechanistic profile. Wide tolerance towards functional groups (27 examples) and application to late-stage functionalization of a bioactive compound (i. e. Colchicine analogue), emphasize the synthetic impact of the present methodology.
Electrochemical Site-Selective Alkylation of Tropones via Formal C(sp3)−C(sp2) Coupling Reaction
Zanardi C.Formal Analysis
;
2024-01-01
Abstract
The first site-selective electrochemical alkylation of tropones is realized by reacting 2-acetoxytropones and redox-active-esters (RAEs). The electroreductive protocol enables the preparation of mono- and disubstituted tropones in high yields (up to 71%) under very mild conditions. Dedicated voltammetric measurements served for the identification of 2-acetoxytropones as a class of valuable trapping agents of nucleophilic radical species and shed light on the whole mechanistic profile. Wide tolerance towards functional groups (27 examples) and application to late-stage functionalization of a bioactive compound (i. e. Colchicine analogue), emphasize the synthetic impact of the present methodology.
I documenti in ARCA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
