ArticleChemistry (Weinheim an der Bergstrasse, Germany)2019
Metal-Free Aryl Cross-Coupling Directed by Traceless Linkers.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- A Photochemical Macrocyclization Route to Asymmetric Strained [3.2] Paracyclophanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Sustainable and highly controlled aryl couplings revealed by systematic assessment of photoactivatable linkers.Chemical science · 2022Article
- Metal-Free Aryl Cross-Coupling Directed by Traceless Linkers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
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8 authors.
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Abstract
The metal-free, highly selective synthesis of biaryls poses a major challenge in organic synthesis. The scope and mechanism of a promising new approach to (hetero)biaryls by the photochemical fusion of aryl substituents tethered to a traceless sulfonamide linker (photosplicing) are reported. Interrogating photosplicing with varying reaction conditions and comparison of diverse synthetic probes (40 examples, including a suite of heterocycles) showed that the reaction has a surprisingly broad scope and involves neither metals nor radicals. Quantum chemical calculations revealed that the C-C bond is formed by an intramolecular photochemical process that involves an excited singlet state and traversal of a five-membered transition state, and thus consistent ipso-ipso coupling results. These results demonstrate that photosplicing is a unique aryl cross-coupling method in the excited state that can be applied to synthesize a broad range of biaryls.
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