التفاصيل البيبلوغرافية
| العنوان: |
Metal‐Free Aryl Cross‐Coupling Directed by Traceless Linkers. |
| المؤلفون: |
Haensch, Veit G., Neuwirth, Toni, Steinmetzer, Johannes, Kloss, Florian, Beckert, Rainer, Gräfe, Stefanie, Kupfer, Stephan, Hertweck, Christian |
| المصدر: |
Chemistry - A European Journal; 12/13/2019, Vol. 25 Issue 70, p16068-16073, 6p |
| مصطلحات موضوعية: |
EXCITED states, ORGANIC synthesis, METALS |
| مستخلص: |
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. [ABSTRACT FROM AUTHOR] |
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| قاعدة البيانات: |
Complementary Index |
