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Visible light amination/Smiles cascade: access to phthalazine derivatives

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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Etienne Brachet, Leyre Marzo, Mohamed Selkti, Burkhard König, Philippe Belmont. Visible light amination/Smiles cascade: access to phthalazine derivatives. Chemical Science , The Royal Society of Chemistry, 2016, 7 (8), pp.5002-5006. ⟨10.1039/C6SC01095D⟩. ⟨hal-02384218⟩

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