Issue 71, 2021

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

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

Supplementary files

Article information

Article type
Communication
Submitted
30 iyl 2021
Accepted
10 avq 2021
First published
11 avq 2021
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2021,57, 8905-8908

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

A. M. Borys, J. M. Gil-Negrete and E. Hevia, Chem. Commun., 2021, 57, 8905 DOI: 10.1039/D1CC04137A

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