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Published on: April 6, 2022
Visible light amination/Smiles cascade: access to phthalazine derivatives
Etienne Brachet1, Leyre Marzo2, Mohamed Selkti3
1Université Sorbonne Paris Cité (USPC) , Université Paris Descartes , Faculté de Pharmacie de Paris , UMR CNRS 8638 (COMETE) , 4 avenue de l'Observatoire , 75006 Paris , France . Email: etienne.brachet@parisdescartes.fr ;
Abstract:
We report the synthesis of various phthalazines via a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical Smiles rearrangement. Phthalazine derivatives are obtained in high yields and from a broad scope readily accessible ortho-alkynylsulfonohydrazone precursors. The mild photoredox conditions ensure an excellent functional group tolerance. Application of this strategy to a one-pot protocol starting from the corresponding carbonyl compounds, and subsequent functionalization allow the rapid synthesis of structurally diverse structures.
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