Discovery of frustrated Lewis pairs: Intermolecular FLPs for activation of small molecules

Topics in Current Chemistry

Volumn 332, Issue , 2013, Pages 1-44

  Stephan, Douglas W ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Alkynes; B H bond activation; C F bond activation; CO2 activation; Frustrated Lewis pairs; Heterolytic activation of disulfide; Heterolytic cleavage of dihydrogen; N2O activation; Olefins; Ring openings

Indexed keywords

EID: 84892608626     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128-2012-381     Document Type: Article

References (129)

1. Lewis GN (1923) Valence and the structure of atoms and molecules. Chemical Catalogue Company, Inc., New York
2. Brown HC, Schlesinger HI, Cardon SZ (1942) Studies in stereochemistry. I. Steric strains as a factor in the relative stability of some coordination compounds of boron. J Am Chem Soc 64:325
3. Wittig G, Benz E (1959) Uber Das Verhalten Von Dehydrobenzol Gegenuber Nucleophilen Und Elektrophilen Reagenzien. Chem Ber-Recl 92:1999
4. Wittig G, Ruckert A (1950) Uber Komplexbildung Mit Triphenylboron .2. Liebigs Ann Chem 566:101
5. Tochtermann W (1966) Structures and reactions of organic ate-complexes. Angew Chem Int Ed 5:351
6. Damico R, Broaddus CD (1966) Hydride transfer. Reactions of triphenylcarbonium fluoroborate and triphenylmethyl bromide with tertiary amines. J Org Chem 31:1607
7. Lankamp H, Nauta WT, Maclean C (1968) A new interpretation of monomer-dimer equilibrium of triphenylmethyl- and alkylsubstituted-diphenyl methyl-radicals in solution. Tetrahedron Lett 2:249
8. Okamoto Y, Shimakaw Y (1970) Synthesis, spectra, and reactions of N-triphenylmethylpyridinium salts - reaction of triphenylmethyl chloride with pyridine under high pressure. J Org Chem 35:3752
9. Doering S, Erker G, Fröhlich R, Meyer O, Bergander K (1998) Reaction of the Lewis acid tris (pentafluorophenyl)borane with a phosphorus ylide: competition between adduct formation and electrophilic and nucleophilic aromatic substitution pathways. Organometallics 17:2183
10. Massey AG, Park AJ (1964) Perfluorophenyl derivatives of the elements. 1. Tris (pentafluorophenyl)boron. J Organomet Chem 2:245
11. Welch GC, Cabrera L, Chase PA, Hollink E, Masuda JD, Wei PR, Stephan DW (2007) Tuning Lewis acidity using the reactivity of "frustrated Lewis pairs": facile formation of phosphine-boranes and cationic phosphonium-boranes. Dalton Trans 3407
12. Welch GC, Juan RRS, Masuda JD, Stephan DW (2006) Reversible, metal-free hydrogen activation. Science 314:1124
13. Welch GC, Holtrichter-Roessmann T, Stephan DW (2008) Thermal rearrangement of phosphine- B(C6F5)3 adducts. Inorg Chem 47:1904
14. Welch GC, Prieto R, Dureen MA, Lough AJ, Labeodan OA, Holtrichter-Rossmann T, Stephan DW (2009) Reactions of phosphines with electron deficient boranes. Dalton Trans 1559
15. Cabrera L, Welch GC, Masuda JD, Wei PR, Stephan DW (2006) Pyridine and phosphine reactions with [CPh3][B(C6F5)4]. Inorg Chim Acta 359:3066
16. Granville SL, Welch GC, Stephan DW (2012) Ni, Pd, Pt and Ru complexes of phosphineborate ligands. Inorg Chem 51:4711
17. Clark TL, Rodezno JM, Clendenning SB, Aouba S, Brodersen PM, Lough AJ, Ruda HE, Manners I (2005) Rhodium-catalyzed dehydrocoupling of fluorinated phosphine-borane adducts: synthesis, characterization, and properties of cyclic and polymeric phosphinoboranes with electron-withdrawing substituents at phosphorus. Chem Eur J 11:4526
18. Jaska CA, Manners I (2004) Heterogeneous or homogeneous catalysis? Mechanistic studies of the rhodium-catalyzed dehydrocoupling of amine-borane and phosphine-borane adducts. J Am Chem Soc 126:9776
19. Yuan Z, Taylor NJ, Marder TB, Williams ID, Kurtz SK, Cheng LT (1990) Three coordinate phosphorus and boron as p-donor and p-Acceptor moieties respectively, in conjugated organic molecules for nonlinear optics; crystal and molecular structures of E-PhCH=CHB(Mes)2, E- 4-MeOC6H4CH=CHB(Mes)2, and E-Ph2PCH=CHB(Mes)2 [Mes = 2,4,6-Me3C6H2]. Chem Commun 1489
20. Yuan Z, Taylor NJ, Sun Y, Marder TB, Williams ID, Cheng L-T (1993) Synthesis and second-order nonlinear optical properties of three coordinate organoboranes with diphenylphosphino and ferrocenyl groups as electron donors: crystal and molecular structures of (E)- DCH=CHB(Mes)2 and DC-C-B(Mes)2 [D = P(C6H5)2, (Z-C5H5)Fe(Z-C5H4); Mes = 2,4,6-(CH3)3C6H2]. J Organomet Chem 449:27
21. Welch GC, Stephan DW (2007) Facile heterolytic cleavage of dihydrogen by phosphines and boranes. J Am Chem Soc 129:1880
22. McCahill JSJ, Welch GC, Stephan DW (2007) Reactivity of "frustrated Lewis pairs": threecomponent reactions of phosphines, a borane, and olefins. Angew Chem Int Ed 46:4968
23. Stephan DW (2008) "Frustrated Lewis pairs": a concept for new reactivity and catalysis. Org Biomol Chem 6:1535
24. Stephan DW (2009) Frustrated Lewis pairs: a new strategy to small molecule activation and hydrogenation catalysis. Dalton Trans 3129
25. Stephan DW (2010) Activation of dihydrogen by non-metal systems. Chem Commun 46:8526
26. Stephan DW, Erker G (2010) Frustrated Lewis pairs: metal-free hydrogen activation and more. Angew Chem Int Ed 49:46
27. 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 5966
28. Jackson RD, James S, Orpen AG, Pringle PG (1993) 1,8- Bis(diphenylphosphino)naphthalene - a rigid chelating, diphosphine analog of proton sponge. J Organomet Chem 458:C3
29. 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 1118
30. Liptau P, Neumann M, Erker G, Kehr G, Frohlich R, Grimme S (2004) Responsive iron neighboring group participation in amino-substituent-stabilized [3]ferrocenophane alphacarbenium ions: a combined theoretical and experimental study. Organometallics 23:21
31. Huber DP, Kehr G, Bergander K, Fröhlich R, Erker G, Tanino S, Ohki Y, Tatsumi K (2008) Heterolytic cleavage of dihydrogen by frustrated Lewis pairs derived from alpha-(dimesitylphosphino) ferrocenes and B(C6F5)3. Organometallics 27:5279
32. Axenov KV, Kehr G, Fröhlich R, Erker G (2009) Catalytic hydrogenation of sensitive organometallic compounds by antagonistic N/B Lewis pair catalyst systems. J Am Chem Soc 131:3454
33. Unverhau K, Lübbe G, Wibbeling B, Fröhlich R, Kehr G, Erker G (2010) Frustrated Lewis pair reactions at the [3]ferrocenophane framework. Organometallics 29:5320
34. Geier SJ, Gilbert TM, Stephan DW (2008) Activation of H2 by phosphinoboranes R2PB (C6F5)2. J Am Chem Soc 130:12632
35. Ullrich M, Lough AJ, Stephan DW (2009) Reversible, metal-free, heterolytic activation of H2 at room temperature. J Am Chem Soc 131:52
36. Ullrich M, Lough AJ, Stephan DW (2010) Dihydrogen activation by B(p-C6F4H)3 and phosphines. Organometallics 29:3647
37. Frey GD, Lavallo V, Donnadieu B, Schoeller WW, Bertrand G (2007) Facile splitting of hydrogen and ammonia by nucleophilic activation at a single carbon center. Science 316:439
38. Chase PA, Gille AL, Gilbert TM, Stephan DW (2009) Frustrated Lewis pairs derived from N-heterocyclic carbenes and Lewis acids. Dalton Trans 7179
39. Chase PA, Stephan DW (2008) Hydrogen and amine activation by a frustrated Lewis pair of a bulky N-heterocyclic carbene and B(C6F5)3. Angew Chem Int Ed 47:7433
40. Holschumacher D, Bannenberg T, Hrib CG, Jones PG, Tamm M (2008) Heterolytic dihydrogen activation by a frustrated carbene-borane Lewis pair. Angew Chem Int Ed 47:7428
41. Chase PA, Jurca T, Stephan DW (2008) Lewis acid-catalyzed hydrogenation: B(C6F5)3- mediated reduction of imines and nitriles with H2. Chem Commun 1701
42. Sumerin V, Schulz F, Nieger M, LeskeläM, Repo T, Rieger B (2008) Facile heterolytic H2 activation by amines and B(C6F5)3. Angew Chem Int Ed 47:6001
43. Piers WE (2005) The chemistry of perfluoroaryl boranes. Adv Organomet Chem 52:1
44. Focante F, Mercandelli P, Sironi A, Resconi L (2006) Complexes of tris(pentafluorophenyl) boron with nitrogen-containing compounds: synthesis, reactivity and metallocene activation. Coord Chem Rev 250:170
45. Geier SJ, Gille AL, Gilbert TM, Stephan DW (2009) From classical adducts to frustrated Lewis pairs: steric effects in the interactions of pyridines and B(C6F5)3. Inorg Chem 48:10466
46. Geier SJ, Stephan DW (2009) Lutidine/B(C6F5)3: at the boundary of classical and frustrated Lewis pair reactivity. J Am Chem Soc 131:3476
47. Roesler R, Har BJN, Piers WE (2002) Synthesis and characterization of (perfluoroaryl) borane-functionalized carbosilane dendrimers and their use as Lewis acid catalysts for the hydrosilation of acetophenone. Organometallics 21:4300
48. Parks DJ, Piers WE (1996) Tris(pentafluorophenyl)boron-catalyzed hydrosilation of aromatic aldehydes, ketones, and esters. J Am Chem Soc 118:9440
49. Blackwell JM, Sonmor ER, Scoccitti T, Piers WE (2000) B(C6F5)3-catalyzed hydrosilation of imines via silyliminium intermediates. Org Lett 2:3921
50. Blackwell JM, Foster KL, Beck VH, Piers WE (1999) B(C6F5)3-catalyzed silation of alcohols: a mild, general method for synthesis of silyl ethers. J Org Chem 64:4887
51. Spence REvH, Piers WE, Sun YM, Parvez M, MacGillivray LR, Zaworotko MJ (1998) Mechanistic aspects of the reactions of bis(pentafluorophenyl)borane with the dialkyl zirconocenes Cp2ZrR2 (R = CH3, CH2SiMe3, and CH2C6H5). Organometallics 17:2459
52. Spence REvH, Parks DJ, Piers WE, Macdonald MA, Zaworotko MJ, Rettig SJ (1995) Competing pathways in the reaction of bis(pentafluorophenyl)borane with bis(Z5-cyclopentadienyl) dimethylzirconium - methane elimination versus methyl-hydride exchange and an example of pentacoordinate carbon. Angew Chem Int Ed 34:1230
53. Piers WE, Chivers T (1997) Pentafluorophenylboranes: from obscurity to applications. Chem Soc Rev 26:345
54. Parks DJ, Spence REvH, Piers WE (1995) Bis(pentafluorophenyl)borane - synthesis, properties, and hydroboration chemistry of a highly electrophilic borane reagent. Angew Chem Int Ed 34:809
55. Parks DJ, Piers WE, Yap GPA (1998) Synthesis, properties, and hydroboration activity of the highly electrophilic borane bis(pentafluorophenyl) borane, HB(C6F5)2. Organometallics 17:5492
56. Parks DJ, Piers WE, Parvez M, Atencio R, Zaworotko MJ (1998) Synthesis and solution and solid-state structures of tris(pentafluorophenyl)borane adducts of PhC(O)X (X = H, Me, OEt, N(iPr)2). Organometallics 17:1369
57. Jacobsen H, Berke H, Döring S, Kehr G, Erker G, Fröhlich R, Meyer O (1999) Lewis acid properties of tris(pentafluorophenyl)borane. Structure and bonding in L-B(C6F5)3 complexes. Organometallics 18:1724
58. Blackwell JM, Morrison DJ, Piers WE (2002) B(C6F5)3 catalyzed hydrosilation of enones and silyl enol ethers. Tetrahedron 58:8247
59. Morrison DJ, Piers WE (2003) Weaker Lewis acid, better catalytic activity: dual mechanisms in perfluoroarylborane-catalyzed allylstannation reactions. Org Lett 5:2857
60. Morrison DJ, Blackwell JM, Piers WE (2004) Mechanistic insights into perfluoroaryl boranecatalyzed allylstannations: toward asymmetric induction with chiral boranes. Pure Appl Chem 76:615
61. Asao N, Ohishi T, Sato K, Yamamoto Y (2002) Lewis acid catalyzed stereoselective hydrosilylation of ketones under the control of sigma-pi chelation. Tetrahedron 58:8195
62. Chandrasekhar S, Chandrashekar G, Babu BN, Vijeender K, Reddy KV (2004) Reductive etherification of carbonyl compounds with alkyl trimethylsilylethers using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3. Tetrahedron Lett 45:5497
63. Chandrasekhar S, Reddy CR, Babu BN (2002) Rapid defunctionalization of carbonyl group to methylene with polymethylhydrosiloxane-B(C6F5)3. J Org Chem 67:9080
64. Bach P, Albright A, Laali KK (2009) Influence of Lewis acid and solvent in the hydrosilylation of aldehydes and ketones with Et3SiH; tris(pentafluorophenyl)borane B (C6F5)3 versus metal triflates [M(OTf)3; M = Sc, Bi, Ga, and Al] - mechanistic implications. Eur J Org Chem 1961
65. Piers WE, Marwitz AJV, Mercier LG (2011) Mechanistic aspects of bond activation with perfluoroarylboranes. Inorg Chem 50:12252
66. Gevorgyan V, Rubin M, Liu JX, Yamamoto Y (2001) A direct reduction of aliphatic aldehyde, acyl chloride, ester, and carboxylic functions into a methyl group. J Org Chem 66:1672
67. Gevorgyan V, Rubin M, Benson S, Liu JX, Yamamoto Y (2000) A novel B(C6F5)3-catalyzed reduction of alcohols and cleavage of aryl and alkyl ethers with hydrosilanes. J Org Chem 65:6179
68. Rubin M, Schwier T, Gevorgyan V (2002) Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins. J Org Chem 67:1936
69. Rubin M, Gevorgyan V (2001) B(C6F5)3-catalyzed allylation of secondary benzyl acetates with allylsilanes. Org Lett 3:2705
70. Imamura K, Yoshikawa E, Gevorgyan V, Sudo T, Asao N, Yamamoto Y (2001) Lewis acidmediated intramolecular addition of silyl enol ethers to internal unactivated alkynes. Can J Chem 79:1624
71. Schwier T, Rubin M, Gevorgyan V (2004) B(C6F5)3-catalyzed allylation of propargyl acetates with allylsilanes. Org Lett 6:1999
72. Rendler S, Oestreich M, Butts CP, Lloyd-Jones GC (2007) Intermolecular chirality transfer from silicon to carbon: interrogation of the two-silicon cycle for Pd-catalyzed hydrosilylation by stereoisotopochemical crossover. J Am Chem Soc 129:502
73. Rendler S, Oestreich M (2008) Conclusive evidence for an SN2-Si mechanism in the B (C6F5)3-catalyzed hydrosilylation of carbonyl compounds: implications for the related hydrogenation. Angew Chem Int Ed 47:5997
74. Oestreich M, Rendler S (2005) "True" chirality transfer from silicon to carbon: asymmetric amplification in a reagent controlled palladium-catalyzed hydrosilylation. Angew Chem Int Ed 44:1661
75. Oestreich M (2007) Silicon-stereogenic silanes in asymmetric catalysis. Synlett 1629
76. Zhao X, Stephan DW (2011) Olefin-borane "van der Waals complexes": intermediates in frustrated Lewis pair addition reactions. J Am Chem Soc 133:12448
77. Stirling A, Hamza A, Rokob TA, Papai I (2008) Concerted attack of frustrated Lewis acid-base pairs on olefinic double bonds: a theoretical study. Chem Commun 3148
78. Guo Y, Li S (2008) A novel addition mechanism for the reaction of "frustrated Lewis pairs" with olefins. Eur J Inorg Chem 2501
79. Herrebout WA, van derVeken BJ (1997) Van der Waals complexes between unsaturated hydrocarbons and boron trifluoride: an infrared and ab initio study of ethene.BF3 and propene.BF3. J Am Chem Soc 119:10446
80. Tarakeshwar P, Kim KS (1999) A theoretical investigation of benzene-AlX3 and ethene-AlX3 (X = H, F, Cl) interactions. J Phys Chem A 103:9116
81. Tarakeshwar P, Lee SJ, Lee JY, Kim KS (1999) Ab initio study of benzene-BX3 (X = H, F, Cl) interactions. J Phys Chem B 103:184
82. Zhao X, StephanDW(2012) Frustrated Lewis pair olefin addition reactions: P-, N-, C- and Hbased nucleophilic additions to an olefin tethered to borane. Chem Sci 3:2123
83. Dureen MA, Stephan DW (2009) Terminal alkyne activation by frustrated and classical Lewis acid/phosphine pairs. J Am Chem Soc 131:8396
84. Dureen MA, Brown CC, Stephan DW (2010) Addition of enamines or pyrroles and B(C6F5)3 "frustrated Lewis pairs" to alkynes. Organometallics 29:6422
85. Dureen MA, Stephan DW (2010) Deprotonation and addition reactions of frustrated Lewis pairs with alkynes. Organometallics 29:6594
86. Caputo CB, Geier SJ, Ouyang EY, Kreitner C, Stephan DW (2012) Chloro- and phenoxyphosphines in frustrated Lewis pair additions to alkynes. Dalton Trans 41:237
87. Zhao X, Stephan DW (2011) Synthesis and reactions of zwitterionic alkynyl-phosphonium borates. Chem Eur J 17:6731
88. Zhao XX, Gilbert TM, Stephan DW (2010) C-C coupling by thermolysis of alkynyl phosphonium borates. Chem Eur J 16:10304
89. Jiang CF, Blacque O, Berke H (2010) Activation of terminal alkynes by frustrated Lewis pairs. Organometallics 29:125
90. Chen C, Kehr G, Fröhlich R, Erker G (2010) Carbon-carbon bond activation by 1,1- carboboration of internal alkynes. J Am Chem Soc 132:13594
91. Chen C, Fröhlich R, Kehr G, Erker G (2010) Remarkably variable reaction modes of frustrated Lewis pairs with non-conjugated terminal diacetylenes. Chem Commun 46:3580
92. Chen C, Eweiner F, Wibbeling B, Fröhlich R, Senda S, Ohki Y, Tatsumi K, Grimme S, Kehr G, Erker G (2010) Exploring the limits of frustrated Lewis pair chemistry with alkynes: detection of a system that favors 1,1-carboboration over cooperative 1,2-P/B-Addition. Chem Asian J 5:2199
93. Breen TL, Stephan DW (1992) Substitution or nucleophilic-Attack by phosphines on ZrCl4(THF)2. Inorg Chem 31:4019
94. Avens LR, Barnhart DM, Burns CJ, McKee SD (1996) Uranium-mediated ring opening of tetrahydrofuran. Crystal structure of UI2(OCH2CH2CH2CH2I)2(Ph3P=O)2. Inorg Chem 35:537
95. Campello MPC, Domingos A, Santos I (1994) Uranium complexes with hydrotris(pyrazolyl) borate. J Organomet Chem 484:37
96. Evans WJ, Leman JT, Ziller JW, Khan SI (1996) Synthesis and reactivity of organosamarium diarylpnictide complexes: cleavage reactions of group 15 E-E and E-C bonds by samarium (II). Inorg Chem 35:4283
97. Mommertz A, Leo R, Massa W, Harms K, Dehnicke K (1998) Synthesis of a titanaoxacyclohexane ring by controlled ring opening of tetrahydrofuran. Crystal structures of [cyclo- (Ti(CH2)4O){Me2Si(NtBu)2}]2, [TiCl{Me2 Si(NtBu)2}]3(m3-O)(m3-Cl), and [Li2(THF)3{Me2Si (NtBu)2}]. Z Anorg Allg Chem 624:1647
98. Guo ZY, Bradley PK, Jordan RF (1992) THF ring-opening and hydrogen/deuterium exchange reactions of (C5H4Me)2Zr(H)(THF)+. Evidence for hydrogenolysis of zirconiumcyclopentadiene bonds. Organometallics 11:2690
99. Polamo M, Mutikainen I, Leskela M (1997) A tetrahydrofuran ring-opening product: transtetrachloro{ 4-[2-(phenylamino)pyridinio]butoxido-O} (tetrahydrofuran-O)zirconium(IV). Acta Crystallogr C C53:1036
100. GomezSaso M, Mullica DF, Sappenfield E, Stone FGA (1996) Reactions of nido- 7,8-C2B9H13 with pentacarbonyl(methyl)manganese: crystal structure of the chargecompensated complex [Mn(CO)(3){n5-7,8-C2B9H10-10-O(CH2)4}]. Polyhedron 15:793
101. Chivers T, Schatte G (2003) Cooperative THF ring-opening by B(C6F5)3 and a tellurium diimide dimer. Eur J Inorg Chem 3314
102. Kunnari SM, Oilunkaniemi R, Laitinen RS, Ahlgren M (2001) An unexpected tetrahydrofuran ring opening: synthesis and structural characterization of Ph3PO(CH2)4TeBr4. J Chem Soc Dalton Trans 3417
103. Campbell JP, Gladfelter WL (1997) Synthesis and structure of alkoxy- and (aryloxy)alanes. Observation of a ring-opening reaction involving tetrahydrofuran. Inorg Chem 36:4094
104. Welch GC, Masuda JD, Stephan DW (2006) Phosphonium-borate zwitterions, anionic phosphines, and dianionic phosphonium-dialkoxides via tetrahydrofuran ring-opening reactions. Inorg Chem 45:478
105. Birkmann B, Voss T, Geier SJ, Ullrich M, Kehr G, Erker G, Stephan DW (2010) Frustrated Lewis pairs and ring-opening of THF, dioxane, and thioxane. Organometallics 29:5310
106. Kaufmann D (1987) Borylation of arylsilanes. 2. Synthesis and reactions of silylated dihalogenphenylboranes. Chem Ber-Recl 120:901
107. Williams VC, Piers WE, Clegg W, Elsegood MRJ, Collins S, Marder TB (1999) New bifunctional perfluoroaryl boranes. Synthesis and reactivity of the ortho-phenylene-bridged diboranes 1,2-[B(C6F5)2]2C6X4 (X = H, F)'. J Am Chem Soc 121:3244
108. Sgro MJ, Dömer J, Stephan DW (2012) Stoichiometric CO2 reductions using a bis-boranebased frustrated Lewis pair. Chem Commun 48:7253-7255
109. Kreitner C, Geier SJ, Stanlake LJE, Caputo C, Stephan DW (2011) Ring openings of lactone and ring contractions of lactide by frustrated Lewis pairs. Dalton Trans 6771
110. Morton JGM, Dureen MA, Stephan DW (2010) Ring-opening of cyclopropanes by "frustrated Lewis pairs". Chem Commun 46:8947
111. Mömming CM, Otten E, Kehr G, Fröhlich R, Grimme S, Stephan DW, Erker G (2009) Reversible metal-free carbon dioxide binding by frustrated Lewis pairs. Angew Chem Int Ed 48:6643
112. Peuser I, Neu RC, Zhao X, Ulrich M, Schirmer B, Tannert JA, Kehr G, Fröhlich R, Grimme S, Erker G, Stephan DW (2011) CO2 and formate complexes of phosphine-borane frustrated Lewis pairs. Chem Eur J 17:9640
113. Neu RC, Menard G, Stephan DW (2012) Exchange chemistry of tBu3P(CO2)B(C6F5)2Cl. Dalton Trans. doi:10.1039/C2DT30206C
114. Zhao X, Stephan DW (2011) Bis-boranes in the frustrated Lewis pair activation of carbon dioxide. Chem Commun 47:1833
115. Ashley AE, Thompson AL, O'Hare D (2009) Non-metal-mediated homogeneous hydrogenation of CO2 to CH3OH. Angew Chem Int Ed 48:9839
116. Tran SD, Tronic TA, Kaminsky W, Heinekey DM, Mayer JM (2011) Metal-free carbon dioxide reduction and acidic C-H activations using a frustrated Lewis pair. Inorg Chim Acta 369:126
117. Menard G, Stephan DW (2010) Room temperature reduction of CO2 to methanol by Al-based frustrated Lewis pairs and ammonia borane. J Am Chem Soc 132:1796
118. Menard G, Stephan DW (2011) Stoichiometric Reduction of CO2 to CO by Al-based frustrated Lewis pairs. Angew Chem Int Ed 51:8396
119. Otten E, Neu RC, Stephan DW (2009) Complexation of nitrous oxide by frustrated Lewis pairs. J Am Chem Soc 131:9918
120. Neu RC, Otten E, Lough A, Stephan DW (2011) The synthesis and exchange chemistry of frustrated Lewis pair-nitrous oxide complexes. Chem Sci 2:170
121. Neu RC, Otten E, Stephan DW (2009) Bridging binding modes of phosphine-stabilized nitrous oxide to Zn(C6F5)2. Angew Chem Int Ed 48:9709
122. Sajid M, Klose A, Birkmann B, Liang L, Kehr G, Lough AJ, Fröhlich R, Daniliuc C, Schirmer B, Grimme S, Stephan DW, Erker G (2012) Reactions of phosphorus/boron frustrated Lewis pairs with SO2. Chem. Sci. doi: 10.1039/C2SC21161K
123. Dureen MA, Welch GC, Gilbert TM, Stephan DW (2009) Heterolytic cleavage of disulfides by frustrated Lewis pairs. Inorg Chem 48:9910
124. Dureen MA, Lough A, Gilbert TM, Stephan DW (2008) B-H activation by frustrated Lewis pairs: borenium or boryl phosphonium cation? Chem Commun 4303
125. Piers WE, Bourke SC, Conroy KD (2005) Borinium, borenium, and boronium ions: synthesis, reactivity, and applications. Angew Chem Int Ed 44:5016
126. Menard G, Stephan DW (2012) C-H activation of isobutylene using frustrated Lewis pairs: aluminum and boron s-Allyl complexes. Angew Chem Int Ed 51:4409
127. Caputo CB, Stephan DW (2012) Activation of alkyl C-F bonds by B(C6F5)3: stoichiometric and catalytic transformations. Organometallics 31:27
128. Rokob TA, Papai I (2012) Hydrogen activation by frustrated Lewis pairs: Insights from computational studies. Top Curr Chem DOI: 10.1007/128-2012-399
129. Schirmer B, Grimme S (2012) Quantum chemistry of FLPs and their activation of small molecules: Methodological aspects. Top Curr Chem DOI: 10.1007/128-2012-389