Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity

Abstract

Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu₃P.HBF₄ gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the reaction of aryl iodides with various 1,2-disubstituetd aryl alkenes.

Graphical Abstract

Keywords:

• 12-Disubstituted aryl alkenes
• ligand effect
• Mizoroki–Heck reaction
• PEG 200/400
• TBABr

Acknowledgments

Financial support is gratefully acknowledged from the CSIR Network Project, ORIGIN – under the XII Five year plan CSC 0108 and PGB thanks the UGC for a SRF.