Synthesis of allylanilines via scandium-catalysed benzylic C(sp3)–H alkenylation with alkynes?

Chemical Communications Pub Date: 2022-05-31 DOI: 10.1039/D2CC02489F

Abstract

The ortho-selective benzylic C(sp3)–H alkenylation of 2-methyl tertiary anilines with internal alkynes has been achieved for the first time by using a half-sandwich scandium catalyst. This protocol provides a straightforward route for the synthesis of a new family of 2-allylaniline derivatives, featuring broad substrate scope, 100% atom-efficiency, high yields, and high chemo-, regio-, and stereoselectivity.

Graphical abstract: Synthesis of allylanilines via scandium-catalysed benzylic C(sp3)–H alkenylation with alkynes
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