Light-Enabled Radical 1,4-Aryl Migration Via a Phospho-Smiles Rearrangement was written by De Abreu, Maxime;Belmont, Philippe;Brachet, Etienne. And the article was included in Journal of Organic Chemistry in 2021.Electric Literature of C15H9ClO The following contents are mentioned in the article:
Rearrangement reactions in organic chem. are attractive strategies to build efficiently complex scaffolds, in just one step, from simple starting materials. Among them, aryl migrations are certainly one of the most useful and straightforward rearrangement for building attractive C-C bonds. Of note, anionic aryl migration reactions were largely described compared to their radical counterparts. Recently, visible-light catalysis proved its efficiency to generate such radical rearrangements due to the concomitant loss of a particle (often CO2 or SO2), which is the driving-force of the reaction. Here, the authors disclose a Smiles-type rearrangement, triggered by a P-containing unit (arylphosphoramidate), therefore called phospho-Smiles rearrangement, allowing a Csp2-Csp2 bond formation thanks to a 1,4-aryl migration reaction. Combining this approach with a radical hydroamination/amination reaction produces an amination/phospho-Smiles cascade particularly attractive, for instance, to study the synthesis of the phthalazine core, a scarcely described scaffold of interest for medicinal chem. projects. This study involved multiple reactions and reactants, such as 5-Chloro-2-(phenylethynyl)benzaldehyde (cas: 1186603-47-3Electric Literature of C15H9ClO).
5-Chloro-2-(phenylethynyl)benzaldehyde (cas: 1186603-47-3) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Electric Literature of C15H9ClO
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics