ABSTRACT
Through ß-activation of alkynoic acid esters with N-heterocyclic carbene catalysis, a formal [3+3] annulation of alkynyl acylazoliums with indolin-3-ones has been developed for the rapid construction of structurally interesting benzofuro[3,2-b]pyridin-2-ones with potential bioactivities. This protocol provides a highly efficient and simple method for the synthesis of the target molecules under mild reaction conditions with a wide substrate scope and excellent chemoselectivity. The synthetic utility of this protocol was also demonstrated by the versatile late-stage modifications.
Subject(s)
Esters , Methane , Catalysis , Methane/analogs & derivativesABSTRACT
An unprecedented N-heterocyclic carbene and magnesium cocatalyzed three-component acylcyanoalkylation of alkenes with cycloketone oxime esters and aldehydes is presented. This method displayed good scope generality, providing a transition-metal- and photoredox-free pathway to access various multifunctionalized aliphatic keto nitrile structures under mild reaction conditions. Moreover, this strategy is supposed to follow a radical relay mechanism via a single electron transfer event of a Mg/matched Breslow intermediate/oxime ester electron-donating acceptor (EDA) complex.
