1,4-Refunctionalization of β-diketones to γ-keto nitriles via C–C single bond cleavage

Qi Wu; Yabo Li; Chenyang Wang; Jianye Zhang; Mengmeng Huang; Jung Keun Kim; Yangjie Wu

doi:10.1039/C8QO00556G

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1,4-Refunctionalization of β-diketones to γ-keto nitriles via C–C single bond cleavage†

Qi Wu,^a Yabo Li,^a Chenyang Wang,^ab Jianye Zhang,^a Mengmeng Huang,^a Jung Keun Kim

*^a and Yangjie Wu

*^a

Author affiliations

* Corresponding authors

^a College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou, P.R. China
E-mail: wyj@zzu.edu.cn, kim@zzu.edu.cn

^b Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
E-mail: chenyang.wang@oc.rwth-aachen.de

Abstract

The 1,4-refunctionalization of β-diketones to γ-keto nitriles was realized via an Fe-catalyzed cascade radical process. The C–C single bond cleavage occurred at the less sterically hindered alkyl ketone side or at the side of β-diarylketones with electron-withdrawing groups. The reaction mechanism was proposed with respect to ESI-MS analysis results.

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DOI: https://doi.org/10.1039/C8QO00556G
Article type: Research Article
Submitted: 06 Jun 2018
Accepted: 11 Jul 2018
First published: 12 Jul 2018

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Org. Chem. Front., 2018,5, 2496-2500

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1,4-Refunctionalization of β-diketones to γ-keto nitriles via C–C single bond cleavage

Q. Wu, Y. Li, C. Wang, J. Zhang, M. Huang, J. K. Kim and Y. Wu, Org. Chem. Front., 2018, 5, 2496 DOI: 10.1039/C8QO00556G

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Organic Chemistry Frontiers

1,4-Refunctionalization of β-diketones to γ-keto nitriles via C–C single bond cleavage†

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1,4-Refunctionalization of β-diketones to γ-keto nitriles via C–C single bond cleavage

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