1 Frustrated Lewis Pair Catalysis: An Introduction
25
86. Chen DJ, Klankermayer J (2008) Metal-Free Catalytic Hydrogenation of Imines with
Tris(perfluorophenyl)borane. Chem Commun 18:2130–2131. https://doi.org/10.1039/B80
1806E
87. Ye KY, Wang XW, Daniliuc CG, Kehr G, Erker G (2017) A Ferrocene-Based Phosphane/Borane Frustrated Lewis Pair for Asymmetric Imine Reduction. Eur J Inorg Chem
2:368–371. https://doi.org/10.1002/ejic.201600834
88. Lindqvist M, Borre K, Axenov K, Kótai B, Nieger M, Leskela M, Pápai I, Repo T (2015)
Chiral Molecular Tweezers: Synthesis and Reactivity in Asymmetric Hydrogenation. J Am
Chem Soc 137(12):4038–4041. https://doi.org/10.1021/ja512658m
89. Liu YB, Du HF (2014) Frustrated Lewis Pair Catalyzed Asymmetric Hydrogenation. Acta
Chim Sinica 72(7):771–777. https://doi.org/10.6023/A14040344
90. Wei SM, Feng XQ, Du HF (2014) A Highly Enantioselective Hydrogenation of Silyl Enol
Ethers Catalyzed by Chiral Frustrated Lewis Pairs. J Am Chem Soc 136(35):12261–12264.
https://doi.org/10.1021/ja507536n
91. Ren XY, Li G, Wei SM, Du HF (2015) Facile Development of Chiral Alkenylboranes From
Chiral Diynes for Asymmetric Hydrogenation of Silyl Enol Ethers. Org Lett 17(4):990–993.
https://doi.org/10.1021/acs.orglett.5b00085
92. Ren X, Du H (2016) Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds. J Am Chem Soc 138(3):810–813. https://doi.org/
10.1021/jacs.5b13104
93. Shang M, Chan JZ, Cao M, Chang Y, Wang Q, Cook B, Torker S, Wasa M (2018) C-H
Functionalization of Amines via Alkene-Derived Nucleophiles Through Cooperative Action
of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis. J Am
Chem Soc 140(33):10593–10601. https://doi.org/10.1021/jacs.8b06699
94. Parks DJ, Piers WE (1996) Tris(pentafluorophenyl)boron-Ccatalyzed Hydrosilation of
Aromatic Aldehydes, Ketones, and Esters. J Am Chem Soc 118:9440–9441. https://doi.org/
10.1021/ja961536g
95. Rendler S, Oestreich M (2008) Conclusive Evidence for an S N 2-Si Mechanism in the
B(C 6 F 5 ) 3 -Catalyzed Hydrosilylation of Carbonyl Compounds: Implications for the Related
Hydrogenation. Angew Chem Int Ed 47(32):5997–6000. https://doi.org/10.1002/anie.200
801675
96. Oestreich M, Hermeke J, Mohr J (2015) A Unified Survey of Si-H and H-H Bond Activation
Catalysed by Electron-Deficient Boranes. Chem Soc Rev 44(8):2202–2220. https://doi.org/
10.1039/c4cs00451e
97. Pérez M, Hounjet LJ, Caputo CB, Dobrovetsky R, Stephan DW (2013) Olefin Isomerization
and Hydrosilylation Catalysis by Lewis Acidic Organofluorophosphonium Salts. J Am Chem
Soc 135(49):18308–18310. https://doi.org/10.1021/Ja410379x
98. Pérez M, Qu ZW, Caputo CB, Podgorny V, Hounjet LJ, Hansen A, Dobrovetsky R,
Grimme S, Stephan DW (2015) Hydrosilylation of Ketones, Imines and Nitriles Catalysed by Electrophilic Phosphonium Cations: Functional Group Selectivity and Mechanistic
Considerations. Chem Eur J 21(17):6491–6500. https://doi.org/10.1002/chem.201406356
99. Augurusa A, Mehta M, Pérez M, Zhu JT, Stephan DW (2016) Catalytic Reduction of Amides
to Amines by Electrophilic Phosphonium Cations via FLP Hydrosilylation. Chem Commun
52(82):12195–12198. https://doi.org/10.1039/c6cc06914b
100. Mehta M, Holthausen MH, Mallov I, Pérez M, Qu ZW, Grimme S, Stephan DW (2015)
Catalytic Ketone Hydrodeoxygenation Mediated by Highly Electrophilic Phosphonium
Cations. Angew Chem Int Ed 54(28):8250–8254. https://doi.org/10.1002/anie.201502579
101. Andrews RJ, Chitnis SS, Stephan DW (2019) Carbonyl and Olefin Hydrosilylation Mediated
by an Air-Stable Phosphorus(III) Dication Under Mild Conditions. Chem Commun 55: 5599–
5602. https://doi.org/10.1039/C9CC02460C
102. Bayne JM, Stephan DW (2016) Phosphorus Lewis Acids: Emerging Reactivity and Applications in Catalysis. Chem Soc Rev 45(4):765–774. https://doi.org/10.1039/c5cs00516g
103. Süsse L, LaFortune JHW, Stephan DW, Oestreich M (2019) Axially Chiral, Electrophilic
Fluorophosphonium Cations: Synthesis, Lewis Acidity, and Reactivity in the Hydrosilylation
of Ketones. Organometallics 38(3):712–721. https://doi.org/10.1021/acs.organomet.8b00912
25
86. Chen DJ, Klankermayer J (2008) Metal-Free Catalytic Hydrogenation of Imines with
Tris(perfluorophenyl)borane. Chem Commun 18:2130–2131. https://doi.org/10.1039/B80
1806E
87. Ye KY, Wang XW, Daniliuc CG, Kehr G, Erker G (2017) A Ferrocene-Based Phosphane/Borane Frustrated Lewis Pair for Asymmetric Imine Reduction. Eur J Inorg Chem
2:368–371. https://doi.org/10.1002/ejic.201600834
88. Lindqvist M, Borre K, Axenov K, Kótai B, Nieger M, Leskela M, Pápai I, Repo T (2015)
Chiral Molecular Tweezers: Synthesis and Reactivity in Asymmetric Hydrogenation. J Am
Chem Soc 137(12):4038–4041. https://doi.org/10.1021/ja512658m
89. Liu YB, Du HF (2014) Frustrated Lewis Pair Catalyzed Asymmetric Hydrogenation. Acta
Chim Sinica 72(7):771–777. https://doi.org/10.6023/A14040344
90. Wei SM, Feng XQ, Du HF (2014) A Highly Enantioselective Hydrogenation of Silyl Enol
Ethers Catalyzed by Chiral Frustrated Lewis Pairs. J Am Chem Soc 136(35):12261–12264.
https://doi.org/10.1021/ja507536n
91. Ren XY, Li G, Wei SM, Du HF (2015) Facile Development of Chiral Alkenylboranes From
Chiral Diynes for Asymmetric Hydrogenation of Silyl Enol Ethers. Org Lett 17(4):990–993.
https://doi.org/10.1021/acs.orglett.5b00085
92. Ren X, Du H (2016) Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds. J Am Chem Soc 138(3):810–813. https://doi.org/
10.1021/jacs.5b13104
93. Shang M, Chan JZ, Cao M, Chang Y, Wang Q, Cook B, Torker S, Wasa M (2018) C-H
Functionalization of Amines via Alkene-Derived Nucleophiles Through Cooperative Action
of Chiral and Achiral Lewis Acid Catalysts: Applications in Enantioselective Synthesis. J Am
Chem Soc 140(33):10593–10601. https://doi.org/10.1021/jacs.8b06699
94. Parks DJ, Piers WE (1996) Tris(pentafluorophenyl)boron-Ccatalyzed Hydrosilation of
Aromatic Aldehydes, Ketones, and Esters. J Am Chem Soc 118:9440–9441. https://doi.org/
10.1021/ja961536g
95. Rendler S, Oestreich M (2008) Conclusive Evidence for an S N 2-Si Mechanism in the
B(C 6 F 5 ) 3 -Catalyzed Hydrosilylation of Carbonyl Compounds: Implications for the Related
Hydrogenation. Angew Chem Int Ed 47(32):5997–6000. https://doi.org/10.1002/anie.200
801675
96. Oestreich M, Hermeke J, Mohr J (2015) A Unified Survey of Si-H and H-H Bond Activation
Catalysed by Electron-Deficient Boranes. Chem Soc Rev 44(8):2202–2220. https://doi.org/
10.1039/c4cs00451e
97. Pérez M, Hounjet LJ, Caputo CB, Dobrovetsky R, Stephan DW (2013) Olefin Isomerization
and Hydrosilylation Catalysis by Lewis Acidic Organofluorophosphonium Salts. J Am Chem
Soc 135(49):18308–18310. https://doi.org/10.1021/Ja410379x
98. Pérez M, Qu ZW, Caputo CB, Podgorny V, Hounjet LJ, Hansen A, Dobrovetsky R,
Grimme S, Stephan DW (2015) Hydrosilylation of Ketones, Imines and Nitriles Catalysed by Electrophilic Phosphonium Cations: Functional Group Selectivity and Mechanistic
Considerations. Chem Eur J 21(17):6491–6500. https://doi.org/10.1002/chem.201406356
99. Augurusa A, Mehta M, Pérez M, Zhu JT, Stephan DW (2016) Catalytic Reduction of Amides
to Amines by Electrophilic Phosphonium Cations via FLP Hydrosilylation. Chem Commun
52(82):12195–12198. https://doi.org/10.1039/c6cc06914b
100. Mehta M, Holthausen MH, Mallov I, Pérez M, Qu ZW, Grimme S, Stephan DW (2015)
Catalytic Ketone Hydrodeoxygenation Mediated by Highly Electrophilic Phosphonium
Cations. Angew Chem Int Ed 54(28):8250–8254. https://doi.org/10.1002/anie.201502579
101. Andrews RJ, Chitnis SS, Stephan DW (2019) Carbonyl and Olefin Hydrosilylation Mediated
by an Air-Stable Phosphorus(III) Dication Under Mild Conditions. Chem Commun 55: 5599–
5602. https://doi.org/10.1039/C9CC02460C
102. Bayne JM, Stephan DW (2016) Phosphorus Lewis Acids: Emerging Reactivity and Applications in Catalysis. Chem Soc Rev 45(4):765–774. https://doi.org/10.1039/c5cs00516g
103. Süsse L, LaFortune JHW, Stephan DW, Oestreich M (2019) Axially Chiral, Electrophilic
Fluorophosphonium Cations: Synthesis, Lewis Acidity, and Reactivity in the Hydrosilylation
of Ketones. Organometallics 38(3):712–721. https://doi.org/10.1021/acs.organomet.8b00912