| Dimethylbut-2-ynedioate mediated esterification of acids via sp(3) C-N bond cleavage of benzylic tertiary amines | |
| Department | OSSO国家重点实验室 |
| 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; Zheng ZJ(郑战江); Xu LW(徐利文) | |
| 2012 | |
| Source Publication | Tetrahedron
 |
| ISSN | 0040-4020 |
| Volume | 68Issue:43Pages:8916-8923 |
| Abstract | 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. |
| Keyword | Esterification C-n Cleavage Acid Tertiary Amine Silanes |
| Subject Area | 物理化学 |
| DOI | 10.1016/j.tet.2012.08.024 |
| Funding Organization | 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) |
| Indexed By | SCI |
| Language | 英语 |
| compositor | 第二作者单位 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.licp.cn/handle/362003/3865 |
| Collection | 羰基合成与选择氧化国家重点实验室（OSSO） |
| Corresponding Author | Zheng ZJ(郑战江); Xu LW(徐利文) |
| Affiliation | 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 |
| Recommended Citation 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.,...&徐利文.(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. |
| Files in This Item: | ||||||
| File Name/Size | DocType | Version | Access | License | ||
| B22.Tetrahedron 68 (（730KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text | |
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