CAS OpenIR
Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes
Jiang, Biao-Lin1,2; Xu, Bao-Hua2; Wang, Meng-Liang1; Li, Zeng-Xi3; Liu, Dian-Sheng1; Zhang, Suo-Jiang2
2018-05-01
Source PublicationASIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN2193-5807
Volume7Issue:5Pages:977-983
AbstractA protocol for a Co-II/N,N',N''-trihydroxyisocyanuric acid (THICA)-catalyzed aerobic oxidative esterification and amidation of aldehydes has been developed. Preliminary insight into the mechanism indicates that such an oxidative C-O/N cross-coupling reaction proceeds by masking the aldehyde in a nucleophilic addition reaction with an alkoxy/amino source, thereby keeping the highly reactive formyl group from undesired oxidation. This protocol for the oxidative esterification and amidation of aldehydes proceeds through two different pathways that are characterized by the intrinsic nucleophilicity of the alkanol and amine sub-strates The former occurs in the presence of p-CH3C6H4SO3H as a cocatalyst and orthoformates as the alkoxy sources, instead of alkanols, to efficiently afford the transient acetals. In contrast, the coupling of the more nucleophilic amines with aldehydes renders a readily accessible cross-coupling reaction that occurs without any cocatalyst but is limited by the potential inhibition of THICA upon nucleophilic substitution by an amine. Consequently, only sterically hindered amines were tolerated in this catalytic system, whereas further condensation occurred in the presence of primary amines to lead to imines.
Keywordamidation cobalt esterification radicals oxidation
DOI10.1002/ajoc.201800118
Language英语
WOS KeywordN-HYDROXYPHTHALIMIDE NHPI ; POLARITY-REVERSAL CATALYST ; HYDROXY PHTHALIMIDE NHPI ; AROMATIC METHYL-ESTERS ; ONE-POT SYNTHESIS ; METAL-FREE ; MILD CONDITIONS ; ALPHA-KETOAMIDES ; BENZYL ALCOHOLS ; AMIDE SYNTHESIS
Funding ProjectNational Natural Science Foundation of China[21476240] ; Instrument Developing Project of the Chinese Academy of Science[YZ201521] ; Chinese Academy of Science 100-Talent Program ; Key Program of National Natural Science Foundation of China[91434203] ; Key Research Program of Frontier Sciences, CAS[QYZDY-SSW-JSC011]
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
Funding OrganizationNational Natural Science Foundation of China ; Instrument Developing Project of the Chinese Academy of Science ; Chinese Academy of Science 100-Talent Program ; Key Program of National Natural Science Foundation of China ; Key Research Program of Frontier Sciences, CAS
WOS IDWOS:000435746300021
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/25042
Collection中国科学院过程工程研究所
Corresponding AuthorXu, Bao-Hua; Liu, Dian-Sheng
Affiliation1.Shanxi Univ, Sch Chem & Chem Engn, Taiyuan 030006, Shanxi, Peoples R China
2.Chinese Acad Sci, State Key Lab Multiphase Complex Syst, Beijing Key Lab Ion Liquids Clean Proc, Key Lab Green Proc & Engn,Inst Proc Engn, Beijing 100190, Peoples R China
3.Grad Univ, Chinese Acad Sci, Coll Chem & Chem Engn, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Jiang, Biao-Lin,Xu, Bao-Hua,Wang, Meng-Liang,et al. Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY,2018,7(5):977-983.
APA Jiang, Biao-Lin,Xu, Bao-Hua,Wang, Meng-Liang,Li, Zeng-Xi,Liu, Dian-Sheng,&Zhang, Suo-Jiang.(2018).Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes.ASIAN JOURNAL OF ORGANIC CHEMISTRY,7(5),977-983.
MLA Jiang, Biao-Lin,et al."Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes".ASIAN JOURNAL OF ORGANIC CHEMISTRY 7.5(2018):977-983.
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