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. 2016 Aug 1;7(8):5002-5006.
doi: 10.1039/c6sc01095d. Epub 2016 May 6.

Visible light amination/Smiles cascade: access to phthalazine derivatives

Etienne Brachet  1 , Leyre Marzo  2 , Mohamed Selkti  3 , Burkhard König  2 , Philippe Belmont  1
Affiliations

Visible light amination/Smiles cascade: access to phthalazine derivatives

Etienne Brachet et al. Chem Sci. .

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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Figures

Fig. 1
Fig. 1. Phthalazines bioactive compounds.
Scheme 1
Scheme 1. State of art in radical hydro- and oxo-amination reactions and in the radical Smiles rearrangement (A and B); our photocatalyzed cascade (C).
Scheme 2
Scheme 2. Functionalization of halogenobenzhydrylphthalazines.
Scheme 3
Scheme 3. Proposed mechanism.
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