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Cobalt-Catalyzed Dehydrogenative Coupling of Alcohols/Aldehydes and Amines: An Important Role for Imine Hydration
Guo, Ya-Fei1,2; Ren, Tian-Lu1; Xu, Bao-Hua1; Wang, Yao-Feng1; Zhang, Suo-Jiang1
2016-04-01
Source PublicationASIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN2193-5807
Volume5Issue:4Pages:568-574
AbstractA cobalt and iodide co-catalyzed oxidative amidation reaction between alcohols or aldehydes and amines has been developed. The reactions proceeded smoothly under mild conditions using tert-butyl hydroperoxide solution in water as the terminal oxidant, with broad functional group tolerance. Mechanistic studies indicated that the tBuO/tBuOO radical generated insitu is the active species responsible for hydrogen abstraction in this catalytic process, and not IO-/IO2-/IO3- ions. Investigation into the reaction mechanism also revealed the potential transiency of a hemiaminal and the important role of its regeneration by imine hydration.
KeywordCobalt Cooperative Catalysis Iodides Iminehydration Oxidative Amidation
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1002/ajoc.201500514
Indexed BySCI
Language英语
WOS KeywordAMIDE BOND FORMATION ; INTRAMOLECULAR SCHMIDT REACTIONS ; DIRECT OXIDATIVE AMIDATION ; N-HYDROXYSUCCINIMIDE ; HYDROCHLORIDE SALTS ; TERTIARY-AMINES ; BENZYL ALCOHOLS ; ALDEHYDES ; MILD ; REARRANGEMENT
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
Funding OrganizationNational Key Basic Research Program of China(2015CB251401) ; National Natural Science Foundation of China(21476240 ; External Cooperation Program of BIC, CAS(GJHZ201306) ; Chinese Academy of Sciences(YZ201521) ; CAS 100-Talent Program ; 91434203)
WOS IDWOS:000374772300018
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/21025
Collection多相复杂系统国家重点实验室
Affiliation1.Chinese Acad Sci, Inst Proc Engn, State Key Lab Multiphase Complex Syst, Beijing Key Lab Ion Liquids Clean Proc,Key Lab Gr, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Coll Chem & Chem Engn, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Guo, Ya-Fei,Ren, Tian-Lu,Xu, Bao-Hua,et al. Cobalt-Catalyzed Dehydrogenative Coupling of Alcohols/Aldehydes and Amines: An Important Role for Imine Hydration[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY,2016,5(4):568-574.
APA Guo, Ya-Fei,Ren, Tian-Lu,Xu, Bao-Hua,Wang, Yao-Feng,&Zhang, Suo-Jiang.(2016).Cobalt-Catalyzed Dehydrogenative Coupling of Alcohols/Aldehydes and Amines: An Important Role for Imine Hydration.ASIAN JOURNAL OF ORGANIC CHEMISTRY,5(4),568-574.
MLA Guo, Ya-Fei,et al."Cobalt-Catalyzed Dehydrogenative Coupling of Alcohols/Aldehydes and Amines: An Important Role for Imine Hydration".ASIAN JOURNAL OF ORGANIC CHEMISTRY 5.4(2016):568-574.
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