1. 毕业设计（论文）的内容和要求
在2007年，Sadighi课题组在炔烃的氢氟上取得了重大进展，通过应用卡宾金的配合物催化活化炔键，用三乙胺三氢氟酸盐作为氟源，实现了炔键的反式氢氟化，然而反应的区域选择性未能得到好的控制。
2009年，Miller课题组通过在炔键周围引入导向官能团来控制反应的区域选择性。
相比于乙酸苯甲氧酯的导向，乙酸三氯甲基乙酯获得了更好的区域选择性。
2. 参考文献
[1] J. Che, Y. Li, F. Zhang, et al. Silver-promoted trans-hydrofluorination of ynamides: a regio- and stereoselective approach to (Z)-α-fluoroenamides. Tetrahedron Lett. 2014, 55(45), 62406242.[2] (a) G. A. Olah, M. Nojima, I. Kerekes, Synthetic methods and reactions. II. Hydrofluorination of alkenes, cyclopropane, and alkynes with poly-hydrogen fluoride pyridine (trialkylamine) reagents. Synthesis 1973, (12), 779-780; (b) S. Thibaudeau, A. Martin-Mingot, M.-P. Jouanneetaud, et al. A novel, facile route to β-fluoroamines by hydrofluorination using superacid HF-SbF5. Chem Commun. 2007, (30), 3198-3200; (c) F. Liu, A. Martin-Mingot, M.-P. Jouanneetaud, et al. Thibaudeau. Substitution effect on the hydrofluorination reaction of unsaturated amines in superacid HF/SbF5. Org. Biomol. Chem. 2009, 7(22), 4789-4797[3] (a) S. Rozen. Elemental fluorine as a legitimate reagent for selective fluorination of organic compounds. Acc. Chem. Res.1988, 21(8), 307-312; (b) M. A. Tius. An unusual synthesis of a spirothioxanthene derivative. Tetrahedron 1995, 51(50), 6605-6631.[4] T. J. Barker, D. L. Boger. Fe(III)/NaBH4-mediated free radical hydrofluorination of unactivated alkenes. J. Am. Chem. Soc. 2012, 134(33), 13588135891.[5] H. Shigehisa, E. Nishi, M. Fujisawa, et al. Cobalt-Catalyzed Hydrofluorination of Unactivated Olefins: A Radical Approach of Fluorine Transfer Org. Lett. 2013, 15(20), 51585161..[6] E. Emer, L. Pfeifer, J. M. Brown, et al. cis-Specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway. Angew. Chem. Int. Ed. 2014, 53(16), 4181-4185[7] J. A. Akana, K. X. Bhattacharyya, P. Muller, et al. Reversible C-F Bond Formation and the Au-Catalyzed Hydrofluorination of Alkynes. J. Am. Chem. Soc. 2007, 129(25), 7736-7737.[8] B. C.Gorske, C. T. Mbofana, S. J. Miller. Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) Catalysis. Org. Lett. 2009, 11(19), 43184321.[9] F. Nahra, S. Patrick, D. Bello, et al. Hydrofluorination of Alkynes Catalyzed by Gold Bifluorides. ChemCatChem. 2015, 7(2), 240244.[10] O. Okoromoba, E. J. Han, G. B Hammond, et al. Designer HF-Based Fluorination Reagent: Highly Regioselective Synthesis of Fluoroalkenes and gem-Difluoromethylene Compounds from Alkynes. J. Am. Chem. Soc. 2014, 136(41), 1438114384.
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