Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes

doi:10.1002/ajoc.201800118

	Cobalt(II)/N,N',N''- Trihydroxyisocyanuric Acid Catalyzed Aerobic Oxidative Esterification and Amidation of Aldehydes
	Jiang, Biao-Lin 1,2; Xu, Bao-Hua 2; Wang, Meng-Liang 1; Li, Zeng-Xi 3; Liu, Dian-Sheng 1; Zhang, Suo-Jiang 2
刊名	ASIAN JOURNAL OF ORGANIC CHEMISTRY
	2018-05-01
卷号	7 期号:5 页码:977-983
关键词	amidation cobalt esterification radicals oxidation
ISSN号	2193-5807
DOI	10.1002/ajoc.201800118
英文摘要	A 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.
资助项目	National 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关键词	N-HYDROXYPHTHALIMIDE NHPI ; POLARITY-REVERSAL CATALYST ; HYDROXY PHTHALIMIDE NHPI ; AROMATIC METHYL-ESTERS ; ONE-POT SYNTHESIS ; METAL-FREE ; MILD CONDITIONS ; ALPHA-KETOAMIDES ; BENZYL ALCOHOLS ; AMIDE SYNTHESIS
WOS研究方向	Chemistry
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000435746300021
资助机构	National 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
内容类型	期刊论文
源URL	[http://ir.ipe.ac.cn/handle/122111/25041]
专题	中国科学院过程工程研究所
通讯作者	Xu, Bao-Hua; Liu, Dian-Sheng
作者单位	1.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
推荐引用方式 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.