- Catalytic hydrogenation with frustrated lewis pairs: Selectivity achieved by size-exclusion design of lewis acids
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Catalytic hydrogenation that utilizes frustrated Lewis pair (FLP) catalysts is a subject of growing interest because such catalysts offer a unique opportunity for the development of transition-metal-free hydrogenations. The aim of our recent efforts is to further increase the functional-group tolerance and chemoselectivity of FLP catalysts by means of size-exclusion catalyst design. Given that hydrogen molecule is the smallest molecule, our modified Lewis acids feature a highly shielded boron center that still allows the cleavage of the hydrogen but avoids undesirable FLP reactivity by simple physical constraint. As a result, greater latitude in substrate scope can be achieved, as exemplified by the chemoselective reduction of α,β-unsaturated imines, ketones, and quinolines. In addition to synthetic aspects, detailed NMR spectroscopic, DFT, and 2H isotopic labeling studies were performed to gain further mechanistic insight into FLP hydrogenation. Copyright
- Eroes, Gabor,Nagy, Krisztina,Mehdi, Hasan,Papai, Imre,Nagy, Peter,Kiraly, Peter,Tarkanyi, Gabor,Soos, Tibor
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supporting information; scheme or table
p. 574 - 585
(2012/03/08)
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- Synthesis and structure of styryl-substituted azines
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New photochromic derivatives of 2-styrylquinoline and 2-styrylquinoxaline were obtained by the condensation of the methyl derivatives of the mentioned heterocycles with substituted benzaldehydes in the presence of basic and acidic catalysts, and also unde
- Gulakova,Sitin,Kuz'Mina,Fedorova
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experimental part
p. 245 - 252
(2011/05/03)
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