Paracyclophane derivatives in frustrated lewis pair chemistry

Topics in Current Chemistry

Volumn 334, Issue , 2013, Pages 81-100

  Greb, Lutz ^a   Paradies, Jan ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

2.2 Paracyclophane; Borane; Frustrated Lewis pair; Hydrogenactivation; Phosphine; Planar chiral; X Ray

Indexed keywords

EID: 84893026729     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128-2012-375     Document Type: Article

References (79)

1. Zheng C, You S-L (2012) Transfer hydrogenation with Hantzsch esters and related organic hydride donors. Chem Soc Rev 41:2498-2518
2. List B (2002) Proline-catalyzed asymmetric reactions. Tetrahedron 58(28):5573-5590
3. Lelais G, MacMillan DWC (2006) Modern strategies in organic catalysis: the advent and development of iminium activation. Aldrichim Acta 39:79-87
4. Erkkila A, Majander I, Pihko PM (2007) Iminium catalysis. Chem Rev 107(12):5416-5470
5. Ouellet SG, Walji AM, MacMillan DWC (2007) Enantioselective organocatalytic transfer hydrogenation reactions using Hantzsch esters. Acc Chem Res 40(12):1327-1339
6. Yang JW, Fonseca MTH, Vignola N, List B (2005) Metal-free, organocatalytic asymmetric transfer hydrogenation of alpha, beta-unsaturated aldehydes. Angew Chem Int Ed 44(1):108-110
7. Angew Chem 117(1):110-112
8. Yang JW, Fonseca MTH, List B (2004) A metal-free transfer hydrogenation: organocatalytic conjugate reduction of alpha, beta-unsaturated aldehydes. Angew Chem Int Ed 43(48):6660-6662
9. Angew Chem 116(48):6829-6832
10. Ouellet SG, Tuttle JB, MacMillan DWC (2005) Enantioselective organocatalytic hydride reduction. J Am Chem Soc 127(1):32-33
11. Li GL, Liang YX, Antilla JC (2007) A vaulted biaryl phosphoric acid-catalyzed reduction of alpha-imino esters: the highly enantioselective preparation of alpha-amino esters. J Am Chem Soc 129(18):5830-5831
12. Kang Q, Zhao ZA, You SL (2008) Asymmetric transfer hydrogenation of beta, gamma-alkynyl alpha-imino esters by a Bronsted acid. Org Lett 10(10):2031-2034
13. Kang Q, Zhao ZA, You SL (2007) Highly enantioselective transfer hydrogenation of alphaimino esters by a phosphoric acid. Adv Synth Catal 349(10):1657-1660
14. Rueping M, Antonchick AR, Theissmann T (2006) A highly enantioselective Bronsted acid catalyzed cascade reaction: organocatalytic transfer hydrogenation of quinolines and their application in the synthesis of alkaloids. Angew Chem Int Ed 45(22):3683-3686
15. Angew Chem 118(22):3765-3768
16. Rueping M, Antonchick AP, Theissmann T (2006) Remarkably low catalyst loading in Bronsted acid catalyzed transfer hydrogenations: enantioselective reduction of benzoxazines, benzothiazines, and benzoxazinones. Angew Chem Int Ed 45(40):6751-6755
17. Angew Chem 118(40):6903-6907
18. Rueping M, Theissmann T, Antonchick AP (2006) Metal-free Bronsted acid catalyzed transfer hydrogenation-new organocatalytic reduction of quinolines. Synlett (7):1071-1074
19. Rueping M, Sugiono E, Azap C, Theissmann T, Bolte M (2005) Enantioselective Bronsted acid catalyzed transfer hydrogenation: organocatalytic reduction of imines. Org Lett 7(17):3781-3783
20. Zhang ZG, Schreiner PR (2007) Thiourea-catalyzed transfer hydrogenation of aldimines. Synlett (9):1455-1457
21. Paradies J, Schneider JF, Lauber MB, Muhr V, Kratzer D (2011) Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins. Org Biomol Chem 9(11):4323-4327
22. Menche D, Hassfeld J, Li J, Menche G, Ritter A, Rudolph S (2006) Hydrogen bond catalyzed direct reductive amination of ketones. Org Lett 8(4):741-744
23. Menche D, Bohm S, Li J, Rudolph S, Zander W (2007) Synthesis of hindered tertiary amines by a mild reductive amination procedure. Tetrahedron Lett 48(3):365-369
24. Menche D, Arikan F (2006) Thiourea-catalyzed direct reductive amination of aldehydes. Synlett (6):841-844
25. Martin NJA, Cheng X, List B (2008) Organocatalytic asymmetric transferhydrogenation of beta-nitroacrylates: accessing beta(2)-amino acids. J Am Chem Soc 130(42):13862-13863
26. Chase PA, Jurca T, Stephan DW (2008) Lewis acid-catalyzed hydrogenation: B(C6F5)3-mediated reduction of imines and nitriles with H2. Chem Commun (14):1701-1703
27. Chase PA, Welch GC, Jurca T, Stephan DW (2007) Metal-free catalytic hydrogenation (vol 46, p 8050, 2007). Angew Chem Int Ed 46(48):9136-9136
28. Erker G (2011) Organometallic frustrated Lewis pair chemistry. Dalton Trans 40(29):7475-7483
29. Welch GC, Juan RRS, Masuda JD, Stephan DW (2006) Reversible, metal-free hydrogen activation. Science 314(5802):1124-1126
30. Wang HD, Fröhlich R, Kehr G, Erker G (2008) Heterolytic dihydrogen activation with the 1,8-bis(diphenylphosphino)-naphthalene/B(C6F5)3 pair and its application for metal-free catalytic hydrogenation of silyl enol ethers. Chem Commun (45):5966-5968
31. Ullrich M, Lough AJ, Stephan DW (2009) Reversible, metal-free, heterolytic activation of H2 at room temperature. J Am Chem Soc 131(1):52-53
32. 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):6001-6003
33. Angew Chem (120):6090-6092
34. 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):14117-14119
35. Sumerin V, Chernichenko K, Nieger M, Leskela M, Rieger B, Repo T (2011) Highly active metal-free catalysts for hydrogenation of unsaturated nitrogen-containing compounds. Adv Synth Catal 353(11-12):2093-2110
36. Schulz F, Sumerin V, Heikkinen S, Pedersen B, Wang C, Atsumi M, Leskela M, Repo T, Pyykko P, Petry W, Rieger B (2011) Molecular hydrogen tweezers: structure and mechanisms by neutron diffraction, NMR, and deuterium labeling studies in solid and solution. J Am Chem Soc 133(50):20245-20257
37. Chase PA, Welch GC, Jurca T, Stephan DW (2007) Metal-free catalytic hydrogenation. Angew Chem Int Ed 46(42):8050-8053
38. Angew Chem 119(42):8196-8199
39. Jiang CF, Blacque O, Fox T, Berke H (2011) Heterolytic cleavage of H2 by frustrated B/N Lewis pairs. Organometallics 30(8):2117-2124
40. Jiang CF, Blacque O, Fox T, Berke H (2011) Reversible, metal-free hydrogen activation by frustrated Lewis pairs. Dalton Trans 40(5):1091-1097
41. Jiang CF, Blacque O, Berke H (2009) Metal-free hydrogen activation and hydrogenation of imines by 1,8-bis(dipentafluorophenylboryl)naphthalene. Chem Commun (37):5518-5520
42. Geier SJ, Chase PA, Stephan DW (2010) Metal-free reductions of N-heterocycles via Lewis acid catalyzed hydrogenation. Chem Commun 46(27):4884-4886
43. Ramos A, Lough AJ, Stephan DW (2009) Activation of H2 by frustrated Lewis pairs derived from mono-and bis-phosphinoferrocenes and B(C6F5)3. Chem Commun (9):1118-1120
44. Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown CC, Heiden ZM, Welch GC, Ullrich M (2011) Metal-free catalytic hydrogenation of polar substrates by frustrated Lewis pairs. Inorg Chem 50(24):12338-12348
45. Stephan DW (2008) "Frustrated Lewis pairs": a concept for new reactivity and catalysis. Org Biomol Chem 6(9):1535-1539
46. Paradies J (2011) [2.2]Paracyclophane derivatives: synthesis and application in catalysis. Synthesis 2011 (23):3749-3766
47. Gibson SE, Knight JD (2003) [2.2]Paracyclophane derivatives in asymmetric catalysis. Org Biomol Chem 1(8):1256-1269
48. Falk FC, Fröhlich R, Paradies J (2011) Coupling of ortho-substituted aryl chlorides with bulky amides. Chem Commun 47(39):11095-11097
49. Pye PJ, Rossen K, Reamer RA, Tsou NN, Volante RP, Reider PJ (1997) A new planar chiral bisphosphine ligand for asymmetric catalysis: highly enantioselective hydrogenations under mild conditions. J Am Chem Soc 119(26):6207-6208
50. Falk FC (2012) Neue Liganden und Katalysatorsysteme auf [2.2]Paracyclophanbasis; Synthese, Anwendung und Untersuchungen von Struktur-Reaktivitätsbeziehungen. Thesis, Karlsruhe Institute of Technology (KIT)
51. El Shaieb K, Narayanan V, Hopf H, Dix I, Fischer A, Jones PG, Ernst L, Ibrom K (2003) 4,15-Diamino[2.2]paracyclophane as a starting material for pseudo-geminally substituted [2.2] paracyclophanes. Eur J Org Chem (3):567-577
52. Greb L, Oña-Burgos P, Kubas A, Falka FC, Breher F, Fink K, Paradies J (2012) [2.2] Paracyclophane derived bisphosphines for the activation of hydrogen by FLPs: application in domino hydrosilylation/hydrogenation of enones. Dalton Trans 40:9056-9060
53. Greb L, Oña-Burgos P, Schirmer B, Grimme S, Stephan DW, Paradies J (2012) Metal-free catalytic olefin hydrogenations: low temperature H2-activation by frustrated Lewis pairs. Angew Chem Int Ed. doi:10.1002/anie.201204007
54. Blackwell JM, Morrison DJ, Piers WE (2002) B(C6F5)3 catalyzed hydrosilation of enones and silyl enol ethers. Tetrahedron 58(41):8247-8254
55. Chang SY, Jiaang WT, Cherng CD, Tang KH, Huang CH, Tsai YM (1997) The scope and limitations of intramolecular radical cyclizations of acylsilanes with alkyl, aryl, and vinyl radicals. J Org Chem 62(26):9089-9098
56. Spies P, Fröhlich R, Kehr G, Erker G, Grimme S (2008) Structural importance of secondary interactions in molecules: origin of unconventional conformations of phosphine-borane adducts. Chem Eur J 14(1):333-343
57. Spies P, Kehr G, Bergander K, Wibbeling B, Fröhlich R, Erker G (2009) Metal-free dihydrogen activation chemistry: structural and dynamic features of intramolecular P/B pairs. Dalton Trans (9):1534-1541
58. Vögtle F (1990) Cyclophan-Chemie : Synthesen, Strukturen, Reaktionen : Einführung und Ü berblick. Teubner Studienbücher Chemie. Teubner, Stuttgart
59. Gleiter R, Hopf H (2004) Modern cyclophane chemistry. Wiley-VCH, Weinheim
60. Cipiciani A, Fringuelli F, Mancini V, Piermatti O, Pizzo F, Ruzziconi R (1997) Synthesis of chiral (R)-4-hydroxy-and (R)-4-halogeno[2.2]paracyclophanes and group polarizability. Optical rotation relationship. J Org Chem 62(11):3744-3747
61. Rowlands GJ (2008) The synthesis of enantiomerically pure [2.2]paracyclophane derivatives. Org Biomol Chem 6(9):1527-1534
62. Hitchcock PB, Rowlands GJ, Parmar R (2005) The synthesis of enantiomerically pure 4-substituted [2.2]paracyclophane derivatives by sulfoxide-metal exchange. Chem Commun (33):4219-4221
63. Horton AD, de With J (1997) Controlled alkene and alkyne insertion reactivity of a cationic zirconium complex stabilized by an open diamide ligand. Organometallics 16(25):5424-5436
64. Blackwell JM, Piers WE, ParvezM(2000) Mechanistic studies on selectivity in the B(C6F5)3-catalyzed allylstannation of aldehydes: is hypercoordination at boron responsible? Org Lett 2(5):695-698
65. Blount JF, Finocchiaro P, Gust D, Mislow K (1973) Conformational analysis of triarylboranes. J Am Chem Soc 95(21):7019-7029
66. Cummings SA, IimuraM, Harlan CJ, Kwaan RJ, Trieu IV, Norton JR, Bridgewater BM, Jäkle F, Sundararaman A, Tilset M (2006) An estimate of the reduction potential of B(C6F5)3 from electrochemical measurements on related mesityl boranes. Organometallics 25(7):1565-1568
67. Mayer U, Gutmann V, Gerger W (1975) The acceptor number - a quantitative empirical parameter for the electrophilic properties of solvents. Monatshefte f Chem 106(6):1235-1257
68. Gutmann V (1976) Solvent effects on the reactivities of organometallic compounds. Coord Chem Rev 18(2):225-255
69. Beckett MA, Brassington DS, Coles SJ, Hursthouse MB (2000) Lewis acidity of tris (pentafluorophenyl)borane: crystal and molecular structure of B(C6F5)3•OPEt3. Inorg Chem Commun 3(10):530-533
70. Britovsek GJP, Ugolotti J, White AJP (2005) From B(C6F5)3 to B(OC6F5)3: synthesis of (C6F5)2BOC6F5 and C6F5B(OC6F5)2 and their relative Lewis acidity. Organometallics 24 (7):1685-1691
71. Childs RF, Mulholland DL, Nixon A (1982) The Lewis acid complexes of a, b-unsaturated carbonyl and nitrile compounds. A nuclear magnetic resonance study. Canadian J Chem 60 (6):801-808
72. Ashley AE, Herrington TJ, Wildgoose GG, Zaher H, Thompson AL, Rees NH, Krämer T, O'Hare D (2011) Separating electrophilicity and Lewis acidity: the synthesis, characterization, and electrochemistry of the electron deficient tris(aryl)boranes B(C6F5)3-n(C6Cl5)n (n = 1-3). J Am Chem Soc 133(37):14727-14740
73. Geier SJ, Stephan DW (2009) Lutidine/B(C6F5)3: at the boundary of classical and frustrated Lewis pair reactivity. J Am Chem Soc 131(10):3476-3477
74. Sumerin V, Schulz F, Nieger M, Leskelä M, Repo T, Rieger B (2008) Einfache heterolytische H2-Aktivierung mit Aminen und B(C6F5)3. Angew Chem 120(32):6090-6092
75. Eros G, Mehdi H, Pápai I, Rokob TA, Király P, Tárkányi G, Soós T (2010) Expanding the scope of metal-free catalytic hydrogenation through frustrated Lewis pair design. Angew Chem 122(37):6709-6713
76. Angew Chem Int Ed (49):6559-6563
77. Müller TE, Mingos DMP (1995) Determination of the Tolman cone angle from crystallographic parameters and a statistical analysis using the crystallographic data base. Transition Met Chem 20(6):533-539
78. Tolman CA (1977) Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis. Chem Rev 77(3):313-348
79. Brown TL, Lee KJ (1993) Ligand steric properties. Coord Chem Rev 128(1-2):89-116