Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity?

Chemical Communications Pub Date: 2021-08-11 DOI: 10.1039/D1CC04137A

Abstract

Exploiting the cooperative action of Lewis acid Zn(C6F5)2 with diarylzinc reagents, the efficient arylation of N,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2 not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr2 species, allowing a limiting 50 mol% to be employed.

Graphical abstract: Atom-efficient transition-metal-free arylation of N,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
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