Making the Least Reactive Electrophile the First in Class: Domino Electrophilic Activation of Amides
作者： Daniel Kaiser , Nuno Maulide
关键词: Domino 、 Organic chemistry 、 Reactive intermediate 、 Amide 、 Electrophile 、 Chemistry 、 High energy
摘要: The electrophilic activation of amides, especially by the action trifluoromethanesulfonic (triflic) anhydride, enables formation highly and reactive intermediates, lending themselves to diverse reaction pathways. This synopsis sets out highlight recent advances in field amide activation, focused on use triflic myriad transformations that can ensue upon addition several classes electrophiles intermittently generated high energy intermediates.
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sci-hub.se 参考文章(69)
William S. Bechara, Inna S. Khazhieva, Elsa Rodriguez, André B. Charette, One-Pot Synthesis of 3,4,5-Trisubstituted 1,2,4-Triazoles via the Addition of Hydrazides to Activated Secondary Amides Organic Letters. ,vol. 17, pp. 1184- 1187 ,(2015) , 10.1021/ACS.ORGLETT.5B00128
Mohammad Movassaghi, Matthew D. Hill, Single‐Step Synthesis of Alkynyl Imines from N‐Vinyl and N‐Aryl Amides Organic Syntheses. pp. 88- 95 ,(2008) , 10.1002/0471264229.OS085.10
Stefan A. Ruider, Nuno Maulide, Strong Bonds Made Weak: Towards the General Utility of Amides as Synthetic Modules. Angewandte Chemie. ,vol. 54, pp. 13856- 13858 ,(2015) , 10.1002/ANIE.201508536
Liana Hie, Noah F. Fine Nathel, Tejas K. Shah, Emma L. Baker, Xin Hong, Yun-Fang Yang, Peng Liu, K. N. Houk, Neil K. Garg, Conversion of amides to esters by the nickel-catalysed activation of amide C–N bonds Nature. ,vol. 524, pp. 79- 83 ,(2015) , 10.1038/NATURE14615
Bo Peng, Danny Geerdink, Nuno Maulide, Electrophilic rearrangements of chiral amides: a traceless asymmetric α-allylation. Journal of the American Chemical Society. ,vol. 135, pp. 14968- 14971 ,(2013) , 10.1021/JA408856P
Nuno Maulide, Xueliang Huang, Sebastian Klimczyk, Charge-Accelerated Sulfonium [3,3]-Sigmatropic Rearrangements Synthesis. ,vol. 44, pp. 175- 183 ,(2012) , 10.1055/S-0031-1289632
C. Schmit, S. Sahraoui-Taleb, E. Differding, C.G. Dehasse-De Lombaert, L. Ghosez, Vicinal alkylation of alkynes. A short route toward Δα,β butenolides, furans and cyclopentenones. Tetrahedron Letters. ,vol. 25, pp. 5043- 5046 ,(1984) , 10.1016/S0040-4039(01)91114-1
H. Slebocka-Tilk, R. S. Brown, Effect of distortion on the hydrolytic reactivity of amides. 2. N-Pyramidalization: decomposition of N-benzoylaziridines in aqueous media Journal of Organic Chemistry. ,vol. 52, pp. 805- 808 ,(1987) , 10.1021/JO00381A019
A. J. Speziale, L. R. Smith, The Reaction of Oxalyl Chloride with Amides. II. Oxazolidinediones and Acyl Isocyanates Journal of Organic Chemistry. ,vol. 28, pp. 1805- 1811 ,(1963) , 10.1021/JO01042A016
Mohammad Movassaghi, Matthew D. Hill, Synthesis of Substituted Pyridine Derivatives via the Ruthenium-Catalyzed Cycloisomerization of 3-Azadienynes Journal of the American Chemical Society. ,vol. 128, pp. 4592- 4593 ,(2006) , 10.1021/JA060626A