Photochemistry
Benzaldehyde photoredox heteroarylates amides and ethers
Open access · cc by · source: Europe PMC
Household CFL light plus benzaldehyde and APS couples heteroarene C–H bonds to amide/ether α-C–H positions without a metal photocatalyst.
Key findings
Near-UV (≈364 nm) from CFLs drives the reaction; 0.5 equiv benzaldehyde can suffice (90%); gram-scale 85% isolated yield; formamide carbonyl C–H and N-alkyl C–H both react (e.g. 88% with 8:1 carbonyl selectivity for N-methylformamide).
Methodology
Authors developed a cross-dehydrogenative coupling using benzaldehyde as a photoabsorber, ammonium persulfate as oxidant, and CFL/black-light irradiation, mapping scope on benzothiazoles/quinolines/amides/ethers and probing mechanism with filters, TEMPO, and substituted benzaldehydes.
Limitations
Partners must be used in large excess, and the method is not a catalytic closed photoredox cycle with a recylable Ir/Ru dye.
How this study connects
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