Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y |
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Authors: | Thibault Thierry Dr Emmanuel Pfund Prof Thierry Lequeux |
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Institution: | Normandie Université, Laboratoire de Chimie Moléculaire et Thioorganique LCMT UMR 6507 ENSICAEN, UNICAEN, CNRS, 6 Bd. du Maréchal Juin, 14050 Caen, France |
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Abstract: | A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle. |
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Keywords: | amines heterocycles photocatalysis photooxidation redox chemistry synthetic methods |
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