Abstract
In this review we present relevant and recent applications of porphyrin derivatives as photocatalysts in organic synthesis, involving both single electron transfer (SET) and energy transfer (ET) mechanistic approaches. We demonstrate that these highly conjugated photosensitizers show increasing potential in photocatalysis since they combine both photo- and electrochemical properties which can substitute available metalloorganic photocatalysts. Batch and continuous-flow approaches are presented highlighting the relevance of enabling technologies for the renewal of porphyrin applications in photocatalysis. Finally, the reaction scale in which the methodologies were developed are highlighted since this is an important parameter in the authors’ opinion.
Highlights
In the last decade, photochemistry has re-emerged as a powerful tool for the scientific community
The use of batch reactors on a large-scale is hampered due to the attenuation effect of photon transport (Bouguer–Lambert–Beer law) [1,2,3]. This effect limits the penetration of photons to only a short distance into the reaction vessel, provoking increases of the reaction time, photocatalyst loading, byproducts, overheating and so on
The most recent approach for artemisinin synthesis was described by Wang, Zhou and co-workers [83,84] using porphyrin-based MOFs to produce singlet oxygen, and repeating
Summary
Photochemistry has re-emerged as a powerful tool for the scientific community. The appearance of porphyrins as photoredox catalysts for C–C bond formation started in 2016 with the report from Gryko’s group on the photoredox α-alkylation of aldehydes with diazo compounds using 1 mol % of TPP or ZnTPP as photocatalyst [10] (Scheme 1), obtaining functionalized aldehydes in 47–90% yields. Zhang and co-workers reported a protocol for an oxidative hydroxylation of arylboronic acids by a reductive quenching using a MOF Sn(IV) porphyrin-containing photocatalyst (UNLPF-12) under visible light irradiation.
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