Issue 6, 2021
From the journal:

Organic Chemistry Frontiers

Intermolecular alkene arylcyanation using BnSCN as a cyanide source via a reductive strategy: access to 3,3-disubstituted oxindoles†

Yunxia Feng,a   Shen Zhao,a   Guopeng Du,a   Shuang Zhang,a   Daopeng Zhang,a   Hui Liu,a   Xinjin Li, ORCID logo a   Yunhui Donga  and  Feng-Gang Sun ORCID logo *a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. China
E-mail: fgsun@sdut.edu.cn

Abstract

Herein, a nickel-catalyzed two-component reductive arylcyanation of aryl (pseudo)halide tethered alkenes using benzyl thiocyanate as the cyanide source via C–S bond activation is developed. Using this protocol, a wide scope of 3,3-disubstituted oxindoles bearing all-carbon quaternary stereocenters are accessible in moderate to excellent yields. The preliminary mechanistic investigations reveal that a Ni(I)/Ni(III) process might be involved in the mechanism.

Graphical abstract: Intermolecular alkene arylcyanation using BnSCN as a cyanide source via a reductive strategy: access to 3,3-disubstituted oxindoles

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Article information

DOI
https://doi.org/10.1039/D0QO01462A
Article type
Research Article
Submitted
23 Nov 2020
Accepted
06 Jan 2021
First published
06 Jan 2021

Org. Chem. Front., 2021,8, 1149-1154

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Intermolecular alkene arylcyanation using BnSCN as a cyanide source via a reductive strategy: access to 3,3-disubstituted oxindoles

Y. Feng, S. Zhao, G. Du, S. Zhang, D. Zhang, H. Liu, X. Li, Y. Dong and F. Sun, Org. Chem. Front., 2021, 8, 1149 DOI: 10.1039/D0QO01462A

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