Issue 6, 2023
From the journal:

Organic Chemistry Frontiers

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

Sajid Imran,a   Yang Liu,a   Yan Li,a   Yu Shui,a   Chun-Hui Yana  and  Hong-Mei Sun ORCID logo *a  

* Corresponding authors

a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, Jiangsu 215123, China
E-mail: sunhm@suda.edu.cn

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

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Article information

DOI
https://doi.org/10.1039/D2QO01905A
Article type
Research Article
Submitted
30 Nov 2022
Accepted
22 Dec 2022
First published
23 Dec 2022

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

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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

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