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Issue 11, 2018
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A metal-free direct C (sp3)–H cyanation reaction with cyanobenziodoxolones

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Abstract

A metal-free protocol of direct C(sp3)–H cyanation with cyanobenziodoxolones functioning as both cyanating reagents and oxidants was developed. Unactivated substrates, such as alkanes, ethers and tertiary amines, were thereby transformed to the corresponding nitriles in moderate to high yields. Mechanistic studies indicated that the cyanation proceeded with two potential pathways, which is highly dependent on the substrates: (1) a free radical case for alkanes and ethers and (2) an oxidative case for tertiary amines.

Graphical abstract: A metal-free direct C (sp3)–H cyanation reaction with cyanobenziodoxolones

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Article information


Submitted
20 Jan 2018
Accepted
22 Feb 2018
First published
23 Feb 2018

Org. Biomol. Chem., 2018,16, 1971-1975
Article type
Paper

A metal-free direct C (sp3)–H cyanation reaction with cyanobenziodoxolones

M. Sun, Y. Wang, B. Xu, X. Ma and S. Zhang, Org. Biomol. Chem., 2018, 16, 1971
DOI: 10.1039/C8OB00173A

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