Regioselective Cross-Coupling of Isatogens with Boronic Acids to Construct 2,2-Disubstituted Indolin-3-one Derivatives

Abstract

Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron “ate” complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with excellent regioselectivity, which exhibit operational simplicity, good functional group tolerance, and a broad substrate scope.

Synthetic Applications of Ambiphilic C‐acylimines in Organic Synthesis

“…Song and colleagues developed a regioselective transition metal‐free, cross‐coupling reaction of isatogens 32 with boronic acids 86 (Scheme 29). [37] This protocol exhibits good functional group tolerance and a broad substrate scope under mild reaction conditions, and it is applicable to a wide range of isatogens, as well as aryl, alkenyl, alkyl boronic acids and alkynyl trifluoroborate salts, making it a practical, scalable, and operationally simple method for the synthesis of 2,2‐disubstituted indolin‐3‐one 87 derivatives.…”