Issue 14, 2022

Nickel(0)-catalysed linear-selective hydroarylation of 2-aminostyrenes with arylboronic acids by a bifunctional temporary directing group strategy

Abstract

We report a nickel(0)-catalyzed linear-selective hydroarylation of 2-aminostyrenes with arylboronic acids using a bifunctional temporary directing group strategy. In the presence of a catalytic amount of commercially available 3,5-dibromosalicylaldehyde, an aldimine intermediate is formed to interact with the nickel(0) catalyst by both chelation from the imino group and nickel-hydride formation from the phenoxy group. With the imino-assisted six-membered metallacycle formation, excellent linear selectivity has been achieved for this redox-neutral hydroarylation reaction.

Graphical abstract: Nickel(0)-catalysed linear-selective hydroarylation of 2-aminostyrenes with arylboronic acids by a bifunctional temporary directing group strategy

Supplementary files

Article information

Article type
Research Article
Submitted
05 Apr 2022
Accepted
27 May 2022
First published
30 May 2022

Org. Chem. Front., 2022,9, 3840-3846

Nickel(0)-catalysed linear-selective hydroarylation of 2-aminostyrenes with arylboronic acids by a bifunctional temporary directing group strategy

Q. Wang, Z. Yan and D. Xing, Org. Chem. Front., 2022, 9, 3840 DOI: 10.1039/D2QO00546H

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