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A metal-free direct C (sp(3))-H cyanation reaction with cyanobenziodoxolones
Sun, Ming-Xue1,2; Wang, Yao-Feng2; Xu, Bao-Hua2; Ma, Xin-Qi1; Zhang, Suo-Jiang2

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.

WOS HeadingsScience & Technology ; Physical Sciences
Indexed BySCI
WOS KeywordBeta-keto-esters ; Electrophilic Cyanation ; Alpha-cyanation ; Tertiary-amines ; Strecker Reaction ; Atom-transfer ; Ebx Reagents ; h Bonds ; Alkynylation ; Oxindoles
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
Funding OrganizationNational Science Foundation of China(21606238 ; Instrument Developing Project of the Chinese Academy of Sciences(YZ201521) ; CAS 100-Talent Program ; 21476240 ; U1662133)
WOS IDWOS:000428222500020
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Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Affiliation1.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
Recommended Citation
GB/T 7714
Sun, Ming-Xue,Wang, Yao-Feng,Xu, Bao-Hua,et al. A metal-free direct C (sp(3))-H cyanation reaction with cyanobenziodoxolones[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2018,16(11):1971-1975.
APA Sun, Ming-Xue,Wang, Yao-Feng,Xu, Bao-Hua,Ma, Xin-Qi,&Zhang, Suo-Jiang.(2018).A metal-free direct C (sp(3))-H cyanation reaction with cyanobenziodoxolones.ORGANIC & BIOMOLECULAR CHEMISTRY,16(11),1971-1975.
MLA Sun, Ming-Xue,et al."A metal-free direct C (sp(3))-H cyanation reaction with cyanobenziodoxolones".ORGANIC & BIOMOLECULAR CHEMISTRY 16.11(2018):1971-1975.
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