Dimethylbut-2-ynedioate mediated esterification of acids via sp(3) C-N bond cleavage of benzylic tertiary amines

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	Dimethylbut-2-ynedioate mediated esterification of acids via sp(3) C-N bond cleavage of benzylic tertiary amines
	Shen H(沈浩)1; Lu X(鲁幸)1; Jiang KZ(蒋可志)1; Yang KF(杨科芳)1; Lu YX(卢一新)3,4; Zheng ZJ(郑战江)1; Lai GQ(来国桥)1; Xu LW(徐利文)1,2
刊名	Tetrahedron
	2012
卷号	68 期号:43 页码:8916-8923
关键词	Esterification C-N cleavage Acid Tertiary amine Silanes
ISSN号	0040-4020
通讯作者	郑战江 ; 徐利文
英文摘要	A straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acids was demonstrated in this manuscript. The present protocol can be regarded as a straightforward synthetic transformation of tertiary amines to the esterification of equimolar amounts of acid. Moreover, the reaction is fundamentally new chemistry for the sp³CeN bond cleavage coupled with esterification. The esterification reaction conditions are very mild and functional group-tolerated, such as hydrosilanes, alcohols, phenol, and amino acids. A mechanism is proposed in which the tertiary amine reacts with dimethyl but-2-ynedioate to form zwitterionic salt, and then the zwitterionic intermediate subsequently accept hydrogen to assist the nucleophilic attack of oxygen atom of carboxyl group at the benzyl group of tertiary amine, while a separate reaction pathway leads to esterification.
学科主题	物理化学
收录类别	SCI
资助信息	the National Natural Science Foundation of China (NSFC, No. 20973051;21173064);Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT, JTAS 2011-01-014);Zhejiang Provincial Natural Science Foundation of China (Q12B020037);Qianjiang talent project of Zhejiang Province of China (No. 2010R0017)
语种	英语
WOS记录号	WOS:000309252200012
公开日期	2013-10-11
内容类型	期刊论文
源URL	[http://210.77.64.217/handle/362003/3865]
专题	兰州化学物理研究所_OSSO国家重点实验室
作者单位	1.Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 310012, Zhejiang, Peoples R China 2.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China 3.Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117543, Singapore 4.Natl Univ Singapore, Inst Life Sci, Med Chem Program, Singapore 117543, Singapore
推荐引用方式 GB/T 7714	Shen H,Lu X,Jiang KZ,et al. Dimethylbut-2-ynedioate mediated esterification of acids via sp(3) C-N bond cleavage of benzylic tertiary amines[J]. Tetrahedron,2012,68(43):8916-8923.
APA	Shen H.,Lu X.,Jiang KZ.,Yang KF.,Lu YX.,...&Xu LW.(2012).Dimethylbut-2-ynedioate mediated esterification of acids via sp(3) C-N bond cleavage of benzylic tertiary amines.Tetrahedron,68(43),8916-8923.
MLA	Shen H,et al."Dimethylbut-2-ynedioate mediated esterification of acids via sp(3) C-N bond cleavage of benzylic tertiary amines".Tetrahedron 68.43(2012):8916-8923.