钯催化N,N-二甲基甲酰胺与胺高效合成甲酰胺
收稿日期: 2018-09-15
修回日期: 2018-11-30
网络出版日期: 2018-12-07
基金资助
国家自然科学基金(Nos.21562010,21601039)资助项目.
Pd-Catalyzed N-Formylation of Amines with N,N-Dimethylformamide
Received date: 2018-09-15
Revised date: 2018-11-30
Online published: 2018-12-07
Supported by
Project supported by the National Natural Science Foundation of China (Nos.21562010,21601039).
报道了一种醋酸钯催化N,N-二甲基甲酰胺(DMF)与各类胺高效合成甲酰胺化合物的方法.该反应体系简单,具有催化效率高,不需要其它溶剂及共催化剂,底物普适范围广的优点,为合成甲酰胺化合物提供了一种快速,实用的方法.
关键词: 醋酸钯; N,N-二甲基甲酰胺(DMF); 胺; N-甲酰化
李春 , 王梦娜 , 陆逊花 , 杨元勇 , 张林 . 钯催化N,N-二甲基甲酰胺与胺高效合成甲酰胺[J]. 有机化学, 2019 , 39(4) : 1109 -1115 . DOI: 10.6023/cjoc201809020
A highly efficient protocol for the transamidation of N,N-dimethylformamide (DMF) and amines has been developed, utilizing a catalytic amount Pd(OAc)2. This methodology has a broad substrate scope for aliphatic, aromatic, and heterocyclic amines. And this process is simple and easily performed without solvent and co-catalyst.
Key words: Pd(OAc)2; N,N-dimethylformamide (DMF); amines; N-formylation
[1] (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437.
(b) Peng, J.-J.; Deng, Y. Q. Chin. J. Org. Chem. 2002, 22, 71(in Chinese)(彭家建, 邓友全, 有机化学, 2002, 22, 71).
[2] Sheehan, J. C.; Yang, D. D. H. J. Am. Chem. Soc. 1958, 80, l154.
[3] (a) Ugi, I. Angew. Chem., Int. Eng1. 1982, 21, 810.
(b) Han, Y.; Cai, L. Tetrahedron Lett. 1997, 38, 5423.
(c) Huang, H. J.; Liu, J. Y.; Ma, E. Z.; Cao, Y. Y. Chin. J. Org. Chem. 2015, 35, 2372(in Chinese).(黄海静, 刘巨艳, 马恩忠, 曹映玉, 有机化学, 2015, 35, 2372.)
[4] (a) Jagtap, S. B.; Tsogoeva, S. B. Chem. Commun. 2006, 4747.
(b) Jones, S.; Warner, C. J. A. Org. Biomol. Chem. 2012, 10, 2189.
[5] Fieser, L. F.; Jones, J. E. Org. Synth. Commun. 1955, Ⅲ, 590.
[6] Blicke, F. F.; Lu, C.-J. J. Am. Chem. Soc. 1952, 74, 3933.
[7] Reddy, P. G.; Kumar, G. D. K.; Baskaran, S. Tetrahedron Lett. 2000, 41, 9149.
[8] Duczek, W.; Deutsch, J.; Vieth, S.; Niclas, H.-J. Synthesis 1996, 37.
[9] Desai, B.; Danks, T. N.; Wagner, G. Tetrahedron Lett. 2005, 46, 955.
[10] (a) Zhang, Q.; Chen, C. J. Saudi Chem. Soc. 2016, 20, 114.
(b) Srinivas, M.; Hudwekar, A. D.; Venkateswarlu, V.; Reddy, G. L. Tetrahedron Lett. 2015, 56, 4775.
(c) Chikkulapalli, A.; Aavula, S. K. Tetrahedron Lett. 2015, 56, 3799.
[11] Nguyen, T. B.; Sorres, J.; Tran, M. Q.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2012, 14, 3202.
[12] Dine, T. M. E.; Evans, D.; Rouden, J.; Blanchet, J. Chem.-Eur. J. 2016, 22, 5894.
[13] Lanigan, R. M.; Starkov, P.; Sheppard, T. D. J. Org. Chem. 2013, 78, 4512.
[14] Sonawane, R. B.; Rasal, N. K. Jagtap, S. V. Org. Lett. 2017, 19, 2078.
[15] Gu, D. W.; Guo, X. X. Tetrahedron 2015, 71, 9117.
/
| 〈 |
|
〉 |