Coexistence of lewis acid and base functions: A generalized view of the frustrated lewis pair concept with novel implications for reactivity

Topics in Current Chemistry

Volumn 334, Issue , 2013, Pages 27-58

  Berke, Heinz ^a   Jiang, Yanfeng ^a   Yang, Xianghua ^a   Jiang, Chunfang ^a   Chakraborty, Subrata ^a   Landwehr, Anne ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Bifunctional catalysis; Bond metathesis; C H activation; Double H transfer; Double H transfer cascade; Frustrated Lewis pair; H2 activation; Hydrogenation; Meerwein Pondorf Verley reduction; Metal free hydrogenation; Transfer hydrogenation

Indexed keywords

EID: 84890788412     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128-2012-400     Document Type: Article

References (54)

1. Welch GC, Juan RRS, Masuda JD, Stephan DW (2006) Reversible, metal-free hydrogen activation. Science 314(5802):1124
2. Grimme S, Kruse H, Goerigk L, Erker G (2010) The mechanism of dihydrogen activation by frustrated Lewis pairs revisited. Angew Chem Int Ed 49(8):1402
3. Stephan DW, Erker G (2010) Frustrated Lewis pairs: metal-free hydrogen activation and more. Angew Chem Int Ed 49(1):46
4. Jiang C, Blacque O, Berke H (2009) Metal-free hydrogen activation and hydrogenation of imines by 1,8-bis(dipentafluorophenylboryl)naphthalene. Chem Commun 37:5518
5. Jiang C, Blacque O, Berke H (2009) Metal-free hydrogen activation by the frustrated Lewis pairs of CIB(C6F5)2 and HB(C6F5)2 and bulky Lewis bases. Organometallics 28:5233
6. Jiang C, Blacque O, Fox T, Berke H (2011) Reversible, metal-free hydrogen activation by frustrated Lewis pairs. Dalton Trans 40:1091
7. Jiang C, Blacque O, Fox T, Berke H (2011) Heterolytic cleavage of H2 by frustrated B/N Lewis pairs. Organomet 30:2117
8. Hamilton CW, Baker RT, Staubitz A, Manners I (2009) B-N compounds for chemical hydrogen storage. Chem Soc Rev 38(1):279
9. Labinger JA, Bercaw JE (2002) Understanding and exploiting C-H bond activation. Nature 417 (6888):507
10. Watson PL (1983) Methane exchange-reactions of lanthanide and early-transition-metal methyl complexes. J Am Chem Soc 105(21):6491
11. Thompson ME, Baxter SM, Bulls R, Burger BJ, Nolan MC, Santsiero BD, Schaefer WP, Bercaw JE (1987) Alpha-bond metathesis for C-H bonds of hydrocarbons and Sc-H, Sc-alyl, Sc-aryl bonds of permethylscandocene derivatives-evidence for noninvolvement of the pi-system in electrophilic activation of aromatic and vinylic C-H bonds. J Am Chem Soc 109(1):203
12. Steigerwald ML, Goddard WA (1984) 2s + 2s reactions at transition-metals. The reactions of D2 with Cl2TiH+, Cl2TiH+, and Cl2ScH. J Am Chem Soc 106(2):308
13. Cundari TR (1992) Methane activation by group-IVB imido complexes. J Am Chem Soc 114(26):10557
14. Cummins CC, Baxter SM, Wolczanski PT (1988) Methane and benzene activation via transient (tert-Bu3SiNH)2Zr=NSi-tert-Bu3. J Am Chem Soc 110(26):8731
15. Noyori R, Ohkuma T (2001) Asymmetric catalysis by architectural and functional molecular engineering: practical chemo-and stereoselective hydrogenation of ketones. Angew Chem Int Ed 40(1):40
16. Chakraborty S, Blacque O, Fox T, Berke H (2012) Cheap metals for nobel tasks: synthesis and catalytic activity of molybdenum and tungsten nitrosyl hydride complexes bearing a triphosphine chelate ligand (submitted)
17. Cui W, Li S, Wayland BB (2007) Factors contributing to one-electron metalloradical activation of ethene and carbon monoxide illustrated by reactions of Co(II), Rh(II), and Ir(II) porphyrins. J Organomet Chem 692(15):3198
18. Zhang XX, Parks GF, Wayland BB (1997) One-electron activation of CO by a rhodium(II) porphyrin bimetalloradical complex and concerted reactions of two (RhCO) units. J Am Chem Soc 119(34):7938
19. Wayland BB, Ba SJ, Sherry AE (1992) Reactions of H2(D2) with rhodium(II) metalloradical-kinetic evidence for a 4-centered transition-state. Inorg Chem 31(1):148
20. Spies P, Frohlich R, Kehr G, Erker G, Grimme S (2008) Structural importance of secondary interactions in molecules: origin of unconventional conformations of phosphine-borane adducts. Chem A Eur J 14(3):779
21. Spies P, Schwendemann S, Lange S, Kehr G, Frohlich R, Erker G (2008) Metal-free catalytic hydrogenation of enamines, imines, and conjugated phosphinoalkenylboranes. Angew Chem Int Ed 47(39):7543
22. Mahdi T, Heiden ZM, Grimme S, Stephan DW (2012) Metal-free aromatic hydrogenation: aniline to cyclohexyl-amine derivatives. J Am Chem Soc 134(9):4088
23. Lindqvist M, Sarnela N, Sumerin V, Chernichenko K, Leskelae M, Repo T (2012) Heterolytic dihydrogen activation by B(C6F5)3 and carbonyl compounds. Dalton Trans 41(15):4310
24. Sumerin V, Schulz F, Nieger M, Leskela M, Repo T, Rieger B (2008) Facile heterolytic H2 activation by amines and B(C6F5)3. Angew Chem Int Ed 47(32):6001
25. Sumerin V, Chernichenko K, Nieger M, Leskelae M, Rieger B, Repo T (2011) Highly active metal-free catalysts for hydrogenation of unsaturated nitrogen-containing compounds. Adv Synth Catal 353(11-12):2093
26. Sumerin V, Schulz F, Atsumi M, Wang C, Nieger M, Leskela M, Repo T, Pyykko P, Rieger B (2008) Molecular tweezers for hydrogen: synthesis, characterization, and reactivity. J Am Chem Soc 130(43):14117
27. Berke H (2010) Conceptual approach to the reactivity of dihydrogen. Chemphyschem 11(9):1837
28. Fernandez I, Sierra MA, Cossio FP (2007) In-plane aromaticity in double group transfer reactions. J Org Chem 72(4):1488
29. Fernandez I, Bickelhaupt FM, Cossio FP (2012) Type-I dyotropic reactions: understanding trends in barriers. Chem Eur J 18(39):12517
30. Arrieta A, de Cozar A, Cossio FP (2011) Cyclic electron delocalization in pericyclic reactions. Curr Org Chem 15(20):3594
31. Robertson APM, Leitao EM, Manners I (2011) Catalytic redistribution and polymerization of diborazanes: unexpected observation of metal-free hydrogen transfer between aminoboranes and amine-boranes. J Am Chem Soc 133(48):19322
32. Leitao EM, Stubbs NE, Robertson APM, Helten H, Cox RJ, Lloyd-Jones GC, Manners I (2012) Mechanism of metal-free hydrogen transfer between amine-boranes and aminoboranes. J Am Chem Soc 134(40):16805-16816
33. Node M, Kajimoto T, Ozeki M (2010) Development of novel asymmetric reactions and their application to the synthesis of natural products. Heterocycles 81(5):1061
34. Budzelaar PHM, Talarico G (2003) Struct Bond (Berlin Germany) 105(Group13, Chemistry III):141
35. Doering WV, Young RW (1950) Partially asymmetric Meerwein-Ponndorf-Verley reactions. J Am Chem Soc 72(1):631
36. Yang X, Zhao L, Fox T, Wang Z-X, Berke H (2010) Transfer hydrogenation of imines with ammonia-borane: a concerted double-hydrogen-transfer reaction. Angew Chem Int Ed 49(11): 2058
37. Yang X, Fox T, Berke H (2012) Synthetic and mechanistic studies of metal-free transfer hydrogenations applying polarized olefins as hydrogen acceptors and amine borane adducts as hydrogen donors. Org Biomol Chem 10(4):852
38. Yang X, Fox T, Berke H (2011) Facile metal free regioselective transfer hydrogenation of polarized olefins with ammonia borane. Chem Commun 47(7):2053
39. Yang X, Fox T, Berke H (2011) Ammonia borane as a metal free reductant for ketones and aldehydes: a mechanistic study. Tetrahedron 67(37):7121
40. Pons V, Baker RT, Szymczak NK, Heldebrandt DJ, Linehan JC, Matus MH, Grant DJ, Dixon DA (2008) Coordination of aminoborane, NH2BH2, dictates selectivity and extent of H2 release in metal-catalysed ammonia borane dehydrogenation. Chem Commun (48):6597
41. Shvo Y, Czarkie D, Rahamim Y, Chodosh DF (1986) A new group of ruthenium complexes-structure and catalysis. J Am Chem Soc 108(23):7400
42. Blum Y, Czarkie D, Rahamim Y, Shvo Y (1985) (Cyclopentadienone)ruthenium carbonyl complexes-a new class of homogeneous hydrogenation catalysts. Organometallics 4(8):1459
43. Comas-Vives A, Ujaque G, Lledos A (2007) Hydrogen transfer to ketones catalyzed by Shvo's ruthenium hydride complex: a mechanistic insight. Organometallics 26:4135
44. Conley BL, Pennington-Boggio MK, Boz E, Williams TJ (2010) Discovery, applications, and catalytic mechanisms of Shvo's catalyst. Chem Rev 110(4):2294
45. Casey CP, Singer SW, Powell DR, Hayashi RK, Kavana M (2001) Hydrogen transfer to carbonyls and imines from a hydroxycyclopentadienyl ruthenium hydride: evidence for concerted hydride and proton transfer. J Am Chem Soc 123(6):1090
46. Casey CP, Strotman NA, Beetner SE, Johnson JB, Priebe DC, Vos TE, Khodavandi B, Guzei IA (2006) The PPh3-substituted hydroxycyclopentadienyl ruthenium hydride 2,5-Ph-2-3,4-tol (2)(eta(5)-C4COH) Ru(CO)(PPh3)H is a more efficient catalyst for hydrogenation of aldehydes. Organometallics 25(5):1230
47. Noyori R, Hashiguchi S (1997) Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Acc Chem Res 30:97
48. Clapman SE, Hazdovic A, Morris RH (2004) Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes. Coord Chem Rev 248:2201
49. Gunanathan C, Milstein D (2011) Metal-ligand cooperation by aromatization-dearomatization: a new paradigm in bond activation and "green" catalysis. Acc Chem Res 44(8):588
50. Ikariya T (2011) Bifunctional transition metal-based molecular catalysts for asymmetric syntheses. Top Organomet Chem 37:31
51. Ikariya T (2011) Chemistry of concerto molecular catalysis based on the metal/NH bifunctionality. Bull Chem Soc Jpn 84(1):1
52. Ikariya T, Blacker AJ (2007) Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular. Acc Chem Res 40(12):1300
53. Ikariya T, Murata K, Noyori R (2006) Bifunctional transition metal-based molecular catalysts for asymmetric syntheses. Org Biomol Chem 4:393
54. Landwehr A, Dudle B, Fox T, Blacque O, Berke H (2012) Bifunctional rhenium complexes for the catalytic transfer-hydrogenation reactions of ketones and imines. Chem Eur J 18(18):5701