A BEt3-Base Catalyst for Amide Reduction with Silane

doi:10.1021/acs.joc.9b00277

	A BEt3-Base Catalyst for Amide Reduction with Silane
	Yao, Wubing 1; Fang, Huaquan 1; He, Qiaoxing1,2 ; Peng, Dongjie 1; Liu, Guixia 1; Huang, Zheng1,2
	2019-05-17
发表期刊	JOURNAL OF ORGANIC CHEMISTRY (IF:3.3[JCR-2023],3.2[5-Year])
ISSN	0022-3263
卷号	84 期号:10 页码:6084-6093
发表状态	已发表
DOI	10.1021/acs.joc.9b00277
摘要	Reported herein is the development of a simple but practical catalytic system for the selective reduction of amides with hydrosilane or hydrosiloxane. Low-cost and readily available triethylborane (1.0 M in THF), in combination with a catalytic amount of an alkali metal base, was found to catalyze the reduction of all three amide classes (tertiary, secondary, and primary amides) to form amines under mild conditions. In addition, the selective transformation of secondary amides to aldimines and primary amides to nitriles can also be achieved by using a proper combination of BEt3 and base. The scope of these BEt3-base-catalyzed amide hydrosilylation reactions has been explored in depth. Preliminary results of mechanistic studies suggest a modified Piers' silane Si-H center dot center dot center dot B activation mode wherein the hydride abstraction by BEt3 is promoted by the coordination of an alkoxide or hydroxide anion to the Si center.
收录类别	SCI ; SCIE ; EI ; CCR
语种	英语
资助项目	Science and Technology Commission of Shanghai Municipality[17JC1401200]
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000468696400009
出版者	AMER CHEMICAL SOC
EI入藏号	20192106952510
EI主题词	Alkali metals ; Amides ; Amines ; Hydrosilylation
EI分类号	Air Pollution Control:451.2 ; Alkali Metals:549.1 ; Organic Compounds:804.1
WOS关键词	METAL-FREE REDUCTION ; TERTIARY AMIDES ; SECONDARY AMIDES ; CHEMOSELECTIVE REDUCTION ; DIRECT TRANSFORMATION ; SELECTIVE REDUCTION ; EFFICIENT SYNTHESIS ; COBALT CATALYSTS ; MILD REDUCTION ; PRIMARY AMINES
原始文献类型	Article
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/45574
专题	物质科学与技术学院_硕士生物质科学与技术学院_特聘教授组_黄正组
通讯作者	Huang, Zheng
作者单位	1.Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem,Ctr Excellence Mo, 345 Lingling Rd, Shanghai 200032, Peoples R China 2.Shanghai Tech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
通讯作者单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Yao, Wubing,Fang, Huaquan,He, Qiaoxing,et al. A BEt3-Base Catalyst for Amide Reduction with Silane[J]. JOURNAL OF ORGANIC CHEMISTRY,2019,84(10):6084-6093.
APA	Yao, Wubing,Fang, Huaquan,He, Qiaoxing,Peng, Dongjie,Liu, Guixia,&Huang, Zheng.(2019).A BEt3-Base Catalyst for Amide Reduction with Silane.JOURNAL OF ORGANIC CHEMISTRY,84(10),6084-6093.
MLA	Yao, Wubing,et al."A BEt3-Base Catalyst for Amide Reduction with Silane".JOURNAL OF ORGANIC CHEMISTRY 84.10(2019):6084-6093.