While
photochemical transformations with sunlight almost exclusively
utilize the UV–vis part of the solar spectrum, the majority
of the photons emitted by the sun have frequencies in the near-infrared
region. Phthalocyanines show high structural similarity to the naturally
occurring light-harvesting porphyrins, chlorins, and mainly bacteriochlorins
and are also known for being efficient and affordable near-infrared
light absorbers as well as triplet sensitizers for the production
of singlet oxygen. Although having been neglected for a long time
in synthetic organic chemistry due to their low solubility and high
tendency toward aggregation, their unique photophysical properties
and chemical robustness make phthalocyanines attractive photocatalysts
for the application in near-infrared-light-driven synthesis strategies.
Herein, we report a cheap, simple, and efficient photocatalytic protocol,
which is easily scalable under continuous-flow conditions. Various
phthalocyanines were studied as near-infrared photosensitizers in
oxidative cyanations of tertiary amines to generate α-aminonitriles,
a synthetically versatile compound class.