Coumarin as a Surrogate for the Protection-group-free Synthesis of o-Hydroxy Stilbenes: Hydrolysis-Decarboxylation-Heck Coupling Reactions in One Pot

The 2-hydroxystyrylbenzene scaffold is found in various compounds that are widely applicable in medicinal chemistry as well as material chemistry. Here, a successful attempt is made to develop a one-pot protocol for the synthesis of 2-hydroxystilbene derivatives via hydrolysis of natural coumarins followed by in situ decarboxylative Heck coupling with haloarenes. Fine tuning of the reaction conditions allowed exclusive formation of 2-hydroxystyrylbenzenes over other possible side products, i. e., benzofuran/substituted coumarins.

Automated summary

This study successfully developed a method for synthesizing 2-hydroxystilbene derivatives, using hydrolysis of natural coumarins followed by in situ decarboxylative Heck coupling with haloarenes. The reaction conditions were fine-tuned to exclusively produce 2-hydroxystyrylbenzenes, avoiding the formation of other possible side products such as benzofuran or substituted coumarins.