Competitive micellar induced substrate selectivity in the Pd mediated heck coupling between iodoaryl substrates and linear acrylic esters in water

• Homogeneous catalysts showing substrate selectivity are rare.
• Significant substrate selectivity was observed in the Heck reaction in water.
• No substrate selectivity was observed for the same reaction in organic solvent.
• In micelles longer lipophilic substrates are favored over shorter ones.

Significant substrate selectivity was observed in the competitive Heck coupling reaction, between iodoaryl substrates and five acrylate esters from methyl to lauryl with Pd(OAc)2 in water, under cationic micellar conditions. While in organic medium the shorter acrylate reacts faster than the longer ones, the opposite trend is observed in the micellar medium because the latter hosts the longer, lipophilic substrates much better than the shorter ones.

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