炔酰胺的氧化三氟甲硫基化反应研究任务书

 2021-10-28 08:10

1. 毕业设计(论文)的内容和要求

2011 年,Skrydstrup,T.课题组成功的实现了在没有过渡金属催化的作用下将乙酰氧基连接在炔酰胺分子上,即可实现α-卤代烯酰胺类分子的合成。

底物首先在卤正离子活化下形成烯亚胺离子中间体,历经乙酰氧基迁移,乙酰基离去,最终形成目标产物。

该反应产率中等到优秀,立体选择性最高可达 95/5以上。

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2. 参考文献

a) S Kramer,S-D Friis,Xin Z et al. Metal-free halonium mediated acetate shifts of ynamides to access α-halo acrylamides/acrylimides[J]. Org Lett, 2011,13,(7):1750~1753.b) N Ghosh,S Nayak,A K Sahoo. Gold(I)-catalyzed 6-endo-Dig hydrative cyclization of an alkyne-tethered ynamide: access to 1,6-dihydropyridin-2(3H)ones[J]. Chem Eur J,2013,19,(29):9428~9433.c) Peng B,Huang X,Xie L G,N Maulide. A Brnsted acid catalyzed redox Arylation[J]. Angew Chem Int Ed,2014,53,(33),8718~8721.d) T Chikugo,Y Yauchi,M Ide et al. Transition metal-free oxidation of ynamides for synthesis of α-keto-imides[J]. Tetrahedron,2014,70,(36): 3988~3993.e) Huang H,Tang L et al. Formation of α-chalcogenyl acrylamides through unprecedented chalcogen-mediated metal-free oxyfunctionalization of ynamides with DMSO as an oxidant[J]. Chem Commun,2016,52,(32):5605~5608.f) Pan F,Li X,Chen X et al. Catalytic ynamide oxidation strategy for the preparation of α-Functionalized Amides[J]. ACS Catal,2016,6,(9):6055~6062.g) Huang H,Fan J,He G et al. Generation of oxazolidine-2,4-diones bearing sulfur-substituted quaternary carbon atoms by oxothiolation/cyclization of ynamides[J]. Chem Eur J,2016, 22,(7):2532~2538.

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