Mechanochemistry
is an alternative for sustainable solvent-free
processes that has taken the big step to become, in the near future,
a useful synthetic method for academia and the fine chemical industry.
The apparatus available, based on ball milling systems possessing
several optimizable variables, requires too many control and optimization
experiments to ensure reproducibility, which has limited its widespread
utilization so far. Herein, we describe the development of an automatic
mechanochemical single-screw device consisting of an electrical motor,
a drill, and a drill chamber. The applicability and versatility of
the new device are demonstrated by the implementation of di- and multicomponent
chemical reactions with high reproducibility, using mechanical action
exclusively. As examples, chalcones, dihydropyrimidinones, dihydropyrimidinethiones,
pyrazoline, and porphyrins, were synthesized with high yields. The
unprecedented sustainability is demonstrated by comparison of EcoScale
and E-factor values of these processes with those
previously described in the literature.
This review article briefly describes the available synthetic approaches for meso-arylporphyrins giving particular emphasis for one-pot nitrobenzene and nitrobenzene/NaY methods regarding the synthesis of meso-halogenated arylporphyrins. The review also describes the relevant applications of these halogenated porphyrins and their metalloporphyrin counterparts, prepared via nitrobenzene method, as photosensitizers for therapy (PDT and PDI), diagnostic (molecular contrast agents) and also for catalytic oxidation and CO2 cycloaddition reactions to epoxides.
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