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

被引：34
|
作者：
Sun, Ming-Xue [1 ,2 ]
Wang, Yao-Feng [2 ]
Xu, Bao-Hua [2 ]
Ma, Xin-Qi [1 ]
Zhang, Suo-Jiang [2 ]
机构：
[1] Henan Univ, Henan Engn Res Ctr Resource & Energy Recovery Was, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China
[2] Chinese Acad Sci, Beijing Key Lab Ion Liquids Clean Proc, CAS Key Lab Green Proc & Engn, State Key Lab Multiphase Complex Syst,Inst Proc E, Beijing 100190, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 11期
基金：
美国国家科学基金会;
关键词：
BETA-KETO-ESTERS; ELECTROPHILIC CYANATION; ALPHA-CYANATION; TERTIARY-AMINES; STRECKER REACTION; ATOM-TRANSFER; EBX REAGENTS; H BONDS; ALKYNYLATION; OXINDOLES;
D O I：
10.1039/c8ob00173a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free protocol of direct C(sp(3))-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.
引用
收藏
页码：1971 / 1975
页数：5
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