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Photochemistry

Benzaldehyde photoredox heteroarylates amides and ethers

Zhang Y, Teuscher KB, Ji H · Chemical science · 2016

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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