Asymmetric Counteranion Directed Catalytic Heck/Tsuji-Trost Annulation of Aryl Iodides and 1,3-Dienes

A chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction of aryl iodides and 1,3-dienes is presented. Chiral indoline derivatives could be afforded with remarkably higher yields and enantioselectivities than our previous chiral ligand-based method. Silver carbonate is employed as both base and halide scavenger to ensure fast and recyclable exchange of the catalytic amount of chiral anions. Fast salt metathesis, as well as the acceleration effect of the chiral anion, could both benefit the stereocontrol of the reaction.

Automated summary

This study presents a chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction, resulting in higher yields and enantioselectivities of chiral indoline derivatives compared to previous methods based on chiral ligands. Silver carbonate functions as both base and halide scavenger, facilitating fast and recyclable exchange of the catalytic amount of chiral anions. The fast salt metathesis and acceleration effect of chiral anions both contribute to the stereocontrol of the reaction.