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

Ming Xue Sun; Yao Feng Wang; Bao Hua Xu; Xin Qi Ma; Suo Jiang Zhang

doi:10.1039/c8ob00173a

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

Ming Xue Sun, Yao Feng Wang, Bao Hua Xu, Xin Qi Ma^*, Suo Jiang Zhang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1971-1975
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	16
Issue number	11
DOIs	https://doi.org/10.1039/c8ob00173a
Publication status	Published - 2018
Externally published	Yes

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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.",

author = "Sun, {Ming Xue} and Wang, {Yao Feng} and Xu, {Bao Hua} and Ma, {Xin Qi} and Zhang, {Suo Jiang}",

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AU - Sun, Ming Xue

AU - Wang, Yao Feng

AU - Xu, Bao Hua

AU - Ma, Xin Qi

AU - Zhang, Suo Jiang

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

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U2 - 10.1039/c8ob00173a

DO - 10.1039/c8ob00173a

M3 - Article

C2 - 29498392

AN - SCOPUS:85044024868

SN - 1477-0520

VL - 16

SP - 1971

EP - 1975

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

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

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