Visible light amination/Smiles cascade: access to phthalazine derivatives. Issue 8 (23rd May 2016)

• Record Type: Journal Article
• Authors: Brachet, Etienne; Marzo, Leyre; Selkti, Mohamed; König, Burkhard; Belmont, Philippe
• Is Part Of: Chemical science. Volume 7:Issue 8(2016:Aug.)
• Page Start: 5002
• Page End: 5006
• Publication Date: 2016-05-23
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6sc01095d
• Languages: English
• ISSNs: 2041-6520

Abstract

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. 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.