Visible light amination/Smiles cascade: access to phthalazine derivatives

Chemical Science
Etienne BrachetPhilippe Belmont

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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Citations

Sep 1, 2018·Chemical Communications : Chem Comm·Min-Hua HuangBo Jiang
Oct 20, 2018·Organic & Biomolecular Chemistry·Atul Kumar Chaturvedi, Namrata Rastogi
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Jul 12, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ingrid Allart-SimonJanos Sapi
Oct 1, 2020·Chemistry : a European Journal·Marie HuynhEtienne Brachet
Jan 14, 2021·The Journal of Organic Chemistry·Maxime De AbreuEtienne Brachet
May 29, 2021·Chemical Society Reviews·Mohammed Latrache, Norbert Hoffmann
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Aug 14, 2021·Chemical Reviews·Xue-Qiang ChuChao-Jun Li
Jun 17, 2020·Journal of the American Chemical Society·Jianming YanJie Wu
Apr 15, 2020·Accounts of Chemical Research·Xiao-Ye YuJia-Rong Chen

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Methods Mentioned

BETA
X-ray
hydroamination

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