Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride

doi:10.1002/ejoc.200500834

	Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride
	Ren, J ; Li, LC ; Liu, JK ; Zhu, HJ ; Pittman, CU
通讯作者	hjzhu@mail.kib.ac.cn
	2006-04-10
发表期刊	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN	1434-193X
期号	8 页码:1991-1999
摘要	The mechanisms for the different chemoselectivities in sodium borohydride reactions with primary, secondary and tertiary amides have been investigated both at the B3LYP/631++G(d,p)//B3LYP/6-31G(d,p) and B3LYP/6-31++G(d,p)// HF/6-31G(d,p) levels of theory. The predicted structures of the key intermediates were then confirmed by experiments. Primary amides generate the corresponding nitriles when treated with sodium borohydride. Nitrile formation occurs by initial proton abstraction from the primary amide's nitrogen atom by a hydride ion, followed by loss of hydrogen and the coordination of the amide nitrogen atom to BH3. Three subsequent steps produce acetonitrile. The computational predictions agree well with the experimental results. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
关键词	Chemoselective Reductions Borohydride Amides B3lyp Transition States
学科领域	Chemistry, Organic
DOI	10.1002/ejoc.200500834
收录类别	SCI
语种	英语
WOS记录号	WOS:000236838800021
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/2843
专题	植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.CAS, Kunming Inst Bot, Organ Synth & Nat Prod Lab, Kunming 650204, Yunnan, Peoples R China 2.Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
推荐引用方式 GB/T 7714	Ren, J,Li, LC,Liu, JK,et al. Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2006(8):1991-1999.
APA	Ren, J,Li, LC,Liu, JK,Zhu, HJ,&Pittman, CU.(2006).Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(8),1991-1999.
MLA	Ren, J,et al."Investigations of different chemoselectivities in primary, secondary and tertiary amide reactions with sodium borohydride".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .8(2006):1991-1999.

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