Dimethylbut-2-ynedioate mediated esterification of acids via sp(3) C-N bond cleavage of benzylic tertiary amines
文献类型：期刊论文
| 作者 | 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
 |
| 出版日期 | 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 sp3 CeN 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 |
| 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. |
入库方式： OAI收割
来源：兰州化学物理研究所
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