A modular autonomous flow reactor combining monitoring technologies with a feedback algorithm is presented for the synthesis of the natural product carpanone. The autonomous self-optimizing system, controlled via MATLAB, was designed as a flexible platform enabling an adaptation of the experimental setup to the specificity of the chemical transformation to be optimized. The reaction monitoring uses either online high pressure liquid chromatography (HPLC) or in-line benchtop nuclear magnetic resonance (NMR) spectroscopy. The custom-made optimization algorithm derived from the Nelder-Mead and golden section search methods performs constrained optimizations of black-box functions in a multidimensional search domain, thereby assuming no a priori knowledge of the chemical reactions. This autonomous self-optimizing system allowed fast and efficient optimizations of the chemical steps leading to carpanone. This contribution is the first example of a multistep synthesis where all discrete steps were optimized with an autonomous flow reactor.

Photochemistry is a tremendous research field offering many synthetic possibilities to chemists. Breakthroughs in this area have been notably driven by the implementation of new classes of photocatalysts. Within this context, Bodipy (Boron-dipyrromethene) dyes possess attractive chemical and physical features such as their modularity, strong absorption under visible light irradiation, good thermal and photochemical stabilities, and high fluorescence quantum yields. As such, this class of compounds has found widespread applications in functionalized materials, biology, medicine, or organic chemistry. From an organic-synthetic point of view, excited states of Bodipy dyes have been harnessed in electron and energy transfer reactions. This minireview collates the relevant literature on the applications of these catalysts in synthetic photochemistry and provides some perspectives of this research area.