Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde

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	Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde
	Li MH(李明浩)1; Gu YL(顾彦龙)1,2
刊名	Advanced Synthesis and Catalysis
	2012
卷号	354 期号:13 页码:2484-2494
关键词	aldehydes C?C activation dimedone iron catalysis reversible alkylation three-component reaction
ISSN号	1615-4150
通讯作者	顾彦龙
英文摘要	The selectivity of a three-component electrophilic reaction of an aldehyde with dimedone and another carbon-based nucleophile could be improved by a reversible alkylation procedure, which involves formation, breaking and regeneration of C-C bonds. In the presence of iron(III) chloride and triphenylphosphine, an analogous C-C bond breaking can be observed in the reaction of 2,3,4,9-tetrahydro-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-1H-xanthen-1-one, in which the fragment of dimedone was replaced by a carbon-based nucleophile. Inspired by this observation, some three-component reactions of salicyldehyde and dimedone were successfully developed by using iron(III) chloride and triphenylphosphine (PPh₃) as catalyst. PPh₃ plays the role of hydrogen bond acceptor, which confers a good flexibility of the substrate by weakening the intramolecular hydrogen bond, allowing thus an easy interaction of the substrate with iron(III) chloride catalyst.
学科主题	物理化学与绿色催化
收录类别	SCI
资助信息	the National Natural Science Foundation of China for financial support (21173089);The Program for new Century Excellent Talents in the University of China (NCET-10-0383);the Chutian Scholar Program of the Hubei Provincial Government;the Specialized Research Fund for the Doctoral Program of Higher Education (20090142120081)
语种	英语
WOS记录号	WOS:000308329300020
公开日期	2013-10-11
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/3812]
专题	兰州化学物理研究所_OSSO国家重点实验室
作者单位	1.Huazhong Univ Sci & Technol HUST, Hubei Key Lab Mat Chem & Serv Failure, Sch Chem & Chem Engn, Inst Phys Chem & Ind Catalysis, Wuhan 430074, Peoples R China 2.Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
推荐引用方式 GB/T 7714	Li MH,Gu YL. Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde[J]. Advanced Synthesis and Catalysis,2012,354(13):2484-2494.
APA	Li MH,&Gu YL.(2012).Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde.Advanced Synthesis and Catalysis,354(13),2484-2494.
MLA	Li MH,et al."Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three-Component Reactions of Dimedone and an Aldehyde".Advanced Synthesis and Catalysis 354.13(2012):2484-2494.