Issue 6, 2023

Nickel-catalyzed tandem isomerization/anti-Markovnikov hydroarylation of unactivated internal alkenes with heteroarenes

Abstract

A tandem isomerization/anti-Markovnikov hydroarylation of unactivated internal alkenes with several types of heteroarenes, including benzimidazoles, indoles, benzofurans, and furans, was realized for the first time by using a catalytic system containing a novel NHC-based heteroleptic Ni(II) complex, Ni(IMXy)[P(OEt)3]Br2 [IMXy = 1,3-bis(4-methoxy-2,6-dimethylphenyl)imidazol-2-ylidene], and a base, KOEt. This tandem transformation allows the flexible synthesis of linear C2-alkylheteroarenes from two simple and easily available feedstock chemicals, unactivated internal alkenes and heteroarenes, in a highly regioselective fashion. The practical utility of this protocol is further highlighted by a scaled-up regioconvergent hydroarylation of the alkene mixture into the same linear product with high yield and regioselectivity.

Graphical abstract: Nickel-catalyzed tandem isomerization/anti-Markovnikov hydroarylation of unactivated internal alkenes with heteroarenes

Associated articles

Supplementary files

Article information

Article type
Research Article
Submitted
30 Nov 2022
Accepted
22 Dec 2022
First published
23 Dec 2022

Org. Chem. Front., 2023,10, 1361-1367

Nickel-catalyzed tandem isomerization/anti-Markovnikov hydroarylation of unactivated internal alkenes with heteroarenes

S. Imran, Y. Liu, Y. Li, Y. Shui, C. Yan and H. Sun, Org. Chem. Front., 2023, 10, 1361 DOI: 10.1039/D2QO01905A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements