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Photochemistry

Slow photogenerated Rh–H prefers aldehydes

Ghosh T, Slanina T, König B · Chemical science · 2015

Open access · cc by · source: Europe PMC

Proflavine plus a Cp*Rh mediator makes dilute Rh(III)–H that reduces aldehydes while ketones wait, unlike fast formate hydride transfer.

Key findings

10 mol% of both catalysts in 1:1 DMF/H2O is optimal; a flow reactor speeds the reaction 5× without losing selectivity. Rh(III)–H appears at 612 nm. Φ = (0.14 ± 0.05)% at 455 nm. Triplet 3PFH+* (~2 μs) is reduced by TEOA to PF·– (~530 nm), which then reduces Rh. Aerated runs still give ~30% via photoionization.

Methodology

Authors optimized PF/Rh cat in DMF/water at 455 nm, screened aldehyde/ketone pairs (including a keto-aldehyde), compared formate-generated Rh–H, and used Stern–Volmer, UV-vis, headspace H2 and pump–probe spectra.

Limitations

Quantum yield is low because of fluorescence, H2 evolution and Rh(II) disproportionation; one bifunctional substrate gives a pinacol side product; imine reductions need dry DMSO/thiourea and are a separate optimisation.

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