Chem· 2026Q1
Taming transient radical couplings by preassembling organophotocatalytic dyads
- 2citations
- Q1SCImago
- 2026year
Short summary
Two organophotocatalytic dyads enable metal-free generation and coupling of transient carbon-centered radicals by non-covalently assembling with radical precursors after photoexcitation.
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Key points
- Developed two organophotocatalytic dyads for metal-free generation and coupling of transient radicals.
- Dyads assemble non-covalently with radical precursors, with reactivity triggered by photoexcitation.
- Modulating dyad donor substituent allows control over two distinct catalytic mechanisms.
- Achieved high efficiency, chemoselectivity, and atom economy in coupling alkenyl/alkynyl radicals with trialkylamines.
- Enabled late-stage functionalization of drug molecules, demonstrating broad product scope.
AI-generated from the title and abstract; the full text is not read.
Abstract
We report two organophotocatalytic dyads with distinct mechanisms that enable metal-free generation—and tame couplings—of transient carbon-centered radical partners. After forming their planar charge-transfer or charge-separated states, the dyads assemble non-covalently with radical precursors, and electron transfer reactivity is triggered by photoexcitation. Modulating the dyad's donor substituent diverts the mechanism from (1) consecutive photoinduced electron transfer via a radical anion catalyst/electron-acceptor substrate binary assembly to (2) a ternary assembly of a charge-separated catalyst and both partner substrates. In both cases, reductively generated alkenyl and alkynyl radicals couple with oxidatively activated trialkylamines in high efficiency, exquisite chemoselectivity, and excellent atom economy without the need for any transition metal co-catalyst—improving the sustainability of cross-couplings. Key to success was the intra-assembly generation and stabilization of transient radicals, preventing homocoupling/decomposition and furnishing a broad scope of products, including late-stage-functionalized drug molecules.
The authors' abstract, as published at the source. Chem, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry