Robot-Assisted Reconstruction and Control of the Pechmann Reaction Network

Abstract

A robotic platform was deployed to map the distributions of products and by-products of the classic Pechmann reaction over a four-dimensional "hyperspace" of conditions. This systematic scan reveals the presence of 15 products of which 11 are unprecedented, including those forming by unusual mechanistic routes. In turn, the knowledge of the hyperspace allows for the deduction of causal relationships between the forming species, ultimately enabling the reconstruction of the underlying reaction network. The hyperspace approach provides a more complete description of organic reactions as dynamic networks which, depending on conditions, can be steered toward different outcomes.

Keywords: Benzofurans; Coumarins; Pechmann reaction; Reaction hyperspace; Reaction mechanisms and robotic synthesis.