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.
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Benzaldehyde photoredox heteroarylates amides and ethers
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Black-light CFL irradiation gave 99% yield versus 60% with a household CFL and 0% in the dark.
The initial results indicated that the near UV region of the CFL emission spectrum (364 nm) contributed to this conversion (entry 3, no reaction in darkness; entry 4, 60% yield, irradiated with a household CFL bulb; and entry 5, 99% yield, irradiated with a black light CFL bulb, UV-A light).
The reaction was run on gram scale in 85% isolated yield.
With these conditions in hand, the reaction was successfully implemented on a gram scale (entry 18, 85% isolated yield).
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.
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