Issue 8, 2016

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.

Graphical abstract: Visible light amination/Smiles cascade: access to phthalazine derivatives

Supplementary files

Article information

Article type
Edge Article
Submitted
09 Mar 2016
Accepted
06 May 2016
First published
06 May 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2016,7, 5002-5006

Visible light amination/Smiles cascade: access to phthalazine derivatives

E. Brachet, L. Marzo, M. Selkti, B. König and P. Belmont, Chem. Sci., 2016, 7, 5002 DOI: 10.1039/C6SC01095D

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