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Synlett 2013; 24(7): 777-780
DOI: 10.1055/s-0032-1318312
DOI: 10.1055/s-0032-1318312
synpacts
Frustrated Lewis Pair Catalyzed Hydrogenations
Weitere Informationen
Publikationsverlauf
Received: 14. Januar 2013
Accepted after revision: 04. Februar 2013
Publikationsdatum:
25. Februar 2013 (online)
Abstract
The frustrated Lewis pair (FLP) catalyzed hydrogenation of organic molecules is discussed. The saturation of polarized double bonds by FLP can be described as the nucleophilic addition of hydrides to the polar double bond prior to proton transfer. In contrast, the hydrogenation of olefins proceeds first by protonation forming a transient carbocation, which is subsequently attacked by the hydride. Both processes give rise for efficient conversion of unsaturated organic compounds by a metal-free methodology employing molecular hydrogen.
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References
- 1a Yang JW, Fonseca MT. H, List B. Angew. Chem. Int. Ed. 2004; 43: 6660
- 1b Yang JW, Fonseca MT. H, Vignola N, List B. Angew. Chem. Int. Ed. 2005; 44: 108
- 2a Ouellet SG, Walji AM, MacMillan DW. C. Acc. Chem. Res. 2007; 40: 1327
- 2b Lelais G, MacMillan DW. C. Aldrichimica Acta 2006; 39: 79
- 2c Ouellet SG, Tuttle JB, MacMillan DW. C. J. Am. Chem. Soc. 2005; 127: 32
- 3a Rueping M, Antonchick AP, Theissmann T. Angew. Chem. Int. Ed. 2006; 45: 6751
- 3b Rueping M, Antonchick AR, Theissmann T. Angew. Chem. Int. Ed. 2006; 45: 3683
- 4a Martin NJ. A, Cheng X, List B. J. Am. Chem. Soc. 2008; 130: 13862
- 4b Martin NJ. A, Ozores L, List B. J. Am. Chem. Soc. 2007; 129: 8976
- 4c Paradies J, Schneider JF, Lauber MB, Muhr V, Kratzer D. Org. Biomol. Chem. 2011; 9: 4323
- 5 Zheng C, You SL. Chem. Soc. Rev. 2012; 41: 2498
- 6 Zhu C, Akiyama T. Adv. Synth. Catal. 2010; 352: 1846
- 7a Chase PA, Welch GC, Jurca T, Stephan DW. Angew. Chem. Int. Ed. 2007; 46: 8050
- 7b Welch GC, Juan RR. S, Masuda JD, Stephan DW. Science 2006; 314: 1124
- 8 Stephan DW. Org. Biomol. Chem. 2008; 6: 1535
- 9 Stephan DW, Erker G. Angew. Chem. Int. Ed. 2010; 49: 46 ; Angew. Chem. 2010, 122, 50
- 10a Peuser I, Neu RC, Zhao XX, Ulrich M, Schirmer B, Tannert JA, Kehr G, Fröhlich R, Grimme S, Erker G, Stephan DW. Chem. Eur. J. 2011; 17: 9640
- 10b Mömming CM, Otten E, Kehr G, Fröhlich R, Grimme S, Stephan DW, Erker G. Angew. Chem. Int. Ed. 2009; 48: 6643 ; Angew. Chem. 2009, 121, 6770
- 11 Otten E, Neu RC, Stephan DW. J. Am. Chem. Soc. 2009; 131: 9918
- 12a Cardenas AJ. P, Culotta BJ, Warren TH, Grimme S, Stute A, Fröhlich R, Kehr G, Erker G. Angew. Chem. Int. Ed. 2011; 50: 7567 ; Angew. Chem. 2011, 123, 7709
- 12b Sajid M, Stute A, Cardenas AJ. P, Culotta BJ, Hepperle JA. M, Warren TH, Schirmer B, Grimme S, Studer A, Daniliuc CG, Fröhlich R, Petersen JL, Kehr G, Erker G. J. Am. Chem. Soc. 2012; 134: 10156
- 13 Sajida M, Klose A, Birkmann B, Liang L, Schirmer B, Wiegand T, Eckert H, Lough AJ, Fröhlich R, Daniliuc CG, Grimme S, Stephan DW, Kehr G, Erker G. Chem. Sci. 2013; 4: 213
- 14 Stephan DW. Org. Biomol. Chem. 2012; 10: 5740
- 15a Grimme S, Kruse H, Goerigk L, Erker G. Angew. Chem. Int. Ed. 2010; 49: 1402 ; Angew. Chem. 2010, 122, 1444
- 15b Rokob TA, Hamza A, Stirling A, Papai I. J. Am. Chem. Soc. 2009; 131: 2029
- 15c Rokob TA, Hamza A, Papai I. J. Am. Chem. Soc. 2009; 131: 10701
- 15d Gao SL, Wu W, Mo YR. J. Phys. Chem. A 2009; 113: 8108
- 16 Hamza A, Stirling A, Rokob TA, Papai I. Int. J. Quantum Chem. 2009; 109: 2416
- 17 Mück-Lichtenfeld C, Grimme S. Dalton Trans. 2012; 41: 9111
- 18 Piers WE, Chivers T. Chem. Soc. Rev. 1997; 26: 345
- 19 Spies P, Erker G, Kehr G, Bergander K, Fröhlich R, Grimme S, Stephan DW. Chem. Commun. 2007; 5072
- 20a Spies P, Schwendemann S, Lange S, Kehr G, Fröhlich R, Erker G. Angew. Chem. Int. Ed. 2008; 47: 7543 ; Angew. Chem. 2008, 120, 7654
- 20b Schwendemann S, Fröhlich R, Kehr G, Erker G. Chem. Sci. 2011; 2: 1842
- 21a Eros G, Nagy K, Mehdi H, Papai I, Nagy P, Kiraly P, Tarkanyi G, Soós T. Chem. Eur. J. 2012; 18: 574
- 21b Eros G, Mehdi H, Papai I, Rokob TA, Kiraly P, Tarkanyi G, Soós T. Angew. Chem. Int. Ed. 2010; 49: 6559 ; Angew. Chem. 2010, 122, 6709
- 21c Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown CC, Heiden ZM, Welch GC, Ullrich M. Inorg. Chem. 2011; 50: 12338
- 21d Erker G. Pure Appl. Chem. 2012; 84: 2203
- 22 Geier SJ, Stephan DW. J. Am. Chem. Soc. 2009; 131: 3476
- 23a Sumerin V, Schulz F, Atsumi M, Wang C, Nieger M, Leskela M, Repo T, Pyykko P, Rieger B. J. Am. Chem. Soc. 2008; 130: 14117
- 23b Sumerin V, Schulz F, Nieger M, Leskela M, Repo T, Rieger B. Angew. Chem. Int. Ed. 2008; 47: 6001 ; Angew. Chem. 2008, 120, 6090
- 24a Wang HD, Fröhlich R, Kehr G, Erker G. Chem. Commun. 2008; 5966
- 24b Greb L, Oña-Burgos P, Kubas A, Falk FC, Breher F, Fink K, Paradies J. Dalton Trans. 2012; 40: 9056
- 24c Soós T. Pure Appl. Chem. 2011; 83: 667
- 24d Reddy JS, Xu B.-H, Mahdi T, Fröhlich R, Kehr G, Stephan DW, Erker G. Organometallics 2012; 31: 5638
- 25a Tang WJ, Zhang XM. Chem. Rev. 2003; 103: 3029
- 25b Nugent TC, El-Shazly M. Adv. Synth. Catal. 2010; 352: 753
- 26a Chen DJ, Wang YT, Klankermayer J. Angew. Chem. Int. Ed. 2010; 49: 9475
- 26b Ghattas G, Chen DJ, Pan FF, Klankermayer J. Dalton Trans. 2012; 41: 9026
- 27 Inés B, Palomas D, Holle S, Steinberg S, Nicasio JA, Alcarazo M. Angew. Chem. Int. Ed. 2012; 51: 12367 ; Angew. Chem. 2012, 124, 12533
- 28 Mahdi T, Heiden ZM, Grimme S, Stephan DW. J. Am. Chem. Soc. 2012; 134: 4088
- 29 Ullrich M, Lough AJ, Stephan DW. J. Am. Chem. Soc. 2009; 131: 52
- 30 Greb L, Oña-Burgos P, Schirmer B, Grimme S, Stephan DW, Paradies J. Angew. Chem. Int. Ed. 2012; 51: 10164 ; Angew. Chem. 2012, 124, 10311
- 31 Segawa Y, Stephan DW. Chem. Commun. 2012; 48: 11963