84
X. Feng et al.
19. Chen D, 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
20. Chen D, Wang Y, Klankermayer J (2010) Enantioselective Hydrogenation with Chiral Frustrated Lewis Pairs. Angew Chem Int Ed 49:9475–9478. https://doi.org/10.1002/anie.201
004525
21. Sumerin V, Chernichenko K, Nieger M, Leskelä M, Rieger B, Repo T (2011) Highly Active
Metal-Free Catalysts for Hydrogenation of Unsaturated Nitrogen-Containing Compounds. Adv
Synth Catal 353:2093–2110. https://doi.org/10.1002/adsc.201100206
22. Ghattas G, Chen D, Pan F, Klankermayer J (2012) Asymmetric Hydrogenation of Imines with
a Recyclable Chiral Frustrated Lewis Pair Catalyst. Dalton Trans 41:9026–9028. https://doi.
org/10.1039/C2DT30536D
23. Heiden ZM, Stephan DW (2011) Metal-Free Diastereoselective Catalytic Hydrogenations
of Imines Using B(C 6 F 5 ) 3 . Chem Commun 47:5729–5731. https://doi.org/10.1039/C1CC10
438A
24. Chen D, Leich V, Pan F, Klankermayer J (2012) Enantioselective Hydrosilylation with Chiral
Frustrated Lewis Pairs. Chem Eur J 18:5184–5187. https://doi.org/10.1002/chem.201200244
25. Mewald M, Fröhlich R, Oestreich M (2011) An Axially Chiral, Electron-Deficient Borane:
Synthesis, Coordination Chemistry, Lewis Acidity, and Reactivity. Chem Eur J 17:9406–
9414. https://doi.org/10.1002/chem.201100724
26. Mewald M, Oestreich M (2012) Illuminating the Mechanism of the Borane-Catalyzed
Hydrosilylation of Imines with Both an Axially Chiral Borane and Silane. Chem Eur J
18:14079–14084. https://doi.org/10.1002/chem.201202693
27. Parks DJ, Piers WE, Yap GPA (1998) Synthesis, Properties, and Hydroboration Activity of
the Highly Electrophilic Borane Bis(pentafluorophenyl)borane, HB(C 6 F 5 ) 2 . Organometallics
17:5492–5503. https://doi.org/10.1021/om980673e
28. Liu Y, Du H (2013) Chiral Dienes as “Ligands” for Borane-Catalyzed Metal-Free Asymmetric
Hydrogenation of Imines. J Am Chem Soc 135:6810–6813. https://doi.org/10.1021/ja4025808
29. Cao Z, Du H (2010) Development of Binaphthyl-Based Chiral Dienes for Rh(I)-Catalyzed
Asymmetrc Arylation of N,N-Dimethylsulamoyl-Protected Aldimines. Org Lett 12:2602–
2605. https://doi.org/10.1021/ol1008087
30. Lindqvist M, Borre K, Axenov K, Kótai B, Nieger M, Leskelä M, Pápai I, Repo T (2015) Chiral
Molecular Tweezers: Synthesis and Reactivity in Asymmetric Hydrogenation. J Am Chem Soc
137:4038–4041. https://doi.org/10.1021/ja512658m
31. Wang X, Kehr G, Daniliuc CG, Erker G (2014) Internal Adduct Formation of Active
Intramolecular C 4 -Bridged Frustrated Phosphane/Borane Lewis Pairs. J Am Chem Soc
136:3293–3303. https://doi.org/10.1021/ja413060u
32. Ye K-Y, Wang X, Daniliuc CG, Kehr G, Erker G (2017) A Ferrocene-Based Phosphane/Borane
Frustrated Lewis Pair for Asymmetric Imine Reduction. Eur J Inorg Chem 368–371. https://
doi.org/10.1002/ejic.201600834
33. Liu X, Liu T, Meng W, Du, H (2018) Asymmetric Hydrogenation of Imines with Chiral AlkeneDerived Boron Lewis Acids. Org Biomol Chem 16:8686–8689. https://doi.org/10.1039/C8O
B02446D
34. Tu X-S, Zeng N-N, Li R-Y, Zhao Y-Q, Xie D-Z, Peng Q, Wang X-C (2018) C 2 -Symmetric
Bicyclic Bisborane Catalysts: Kinetic or Thermodynamic Products of a Reversible Hydroboration of Dienes. Angew Chem Int Ed 57:15096–15100. https://doi.org/10.1002/anie.201
808289
35. Lam J, Günther BAR, Farrell JM, Eisenberger P, Bestvater BP, Newman PD, Melen RL,
Crudden CM, Stephan DW (2016) Chiral Carbene-Borane Adducts: Precursors for Borenium
Catalysts for Asymmetric FLP Hydrogenations. Dalton Trans 45:15303–15316. https://doi.
org/10.1039/C6DT02202B
36. Mercea DM, Howlett MG, Piascik AD, Scott DJ, Steven A, Ashley AE, Fuchter MJ (2019)
Enantioselective Reduction of N-Alkyl Ketimines with Frustrated Lewis Pair Catalysis Using
Chiral Borenium Ions. Chem Commun 55:7077–7080. https://doi.org/10.1039/C9CC02900A
X. Feng et al.
19. Chen D, 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
20. Chen D, Wang Y, Klankermayer J (2010) Enantioselective Hydrogenation with Chiral Frustrated Lewis Pairs. Angew Chem Int Ed 49:9475–9478. https://doi.org/10.1002/anie.201
004525
21. Sumerin V, Chernichenko K, Nieger M, Leskelä M, Rieger B, Repo T (2011) Highly Active
Metal-Free Catalysts for Hydrogenation of Unsaturated Nitrogen-Containing Compounds. Adv
Synth Catal 353:2093–2110. https://doi.org/10.1002/adsc.201100206
22. Ghattas G, Chen D, Pan F, Klankermayer J (2012) Asymmetric Hydrogenation of Imines with
a Recyclable Chiral Frustrated Lewis Pair Catalyst. Dalton Trans 41:9026–9028. https://doi.
org/10.1039/C2DT30536D
23. Heiden ZM, Stephan DW (2011) Metal-Free Diastereoselective Catalytic Hydrogenations
of Imines Using B(C 6 F 5 ) 3 . Chem Commun 47:5729–5731. https://doi.org/10.1039/C1CC10
438A
24. Chen D, Leich V, Pan F, Klankermayer J (2012) Enantioselective Hydrosilylation with Chiral
Frustrated Lewis Pairs. Chem Eur J 18:5184–5187. https://doi.org/10.1002/chem.201200244
25. Mewald M, Fröhlich R, Oestreich M (2011) An Axially Chiral, Electron-Deficient Borane:
Synthesis, Coordination Chemistry, Lewis Acidity, and Reactivity. Chem Eur J 17:9406–
9414. https://doi.org/10.1002/chem.201100724
26. Mewald M, Oestreich M (2012) Illuminating the Mechanism of the Borane-Catalyzed
Hydrosilylation of Imines with Both an Axially Chiral Borane and Silane. Chem Eur J
18:14079–14084. https://doi.org/10.1002/chem.201202693
27. Parks DJ, Piers WE, Yap GPA (1998) Synthesis, Properties, and Hydroboration Activity of
the Highly Electrophilic Borane Bis(pentafluorophenyl)borane, HB(C 6 F 5 ) 2 . Organometallics
17:5492–5503. https://doi.org/10.1021/om980673e
28. Liu Y, Du H (2013) Chiral Dienes as “Ligands” for Borane-Catalyzed Metal-Free Asymmetric
Hydrogenation of Imines. J Am Chem Soc 135:6810–6813. https://doi.org/10.1021/ja4025808
29. Cao Z, Du H (2010) Development of Binaphthyl-Based Chiral Dienes for Rh(I)-Catalyzed
Asymmetrc Arylation of N,N-Dimethylsulamoyl-Protected Aldimines. Org Lett 12:2602–
2605. https://doi.org/10.1021/ol1008087
30. Lindqvist M, Borre K, Axenov K, Kótai B, Nieger M, Leskelä M, Pápai I, Repo T (2015) Chiral
Molecular Tweezers: Synthesis and Reactivity in Asymmetric Hydrogenation. J Am Chem Soc
137:4038–4041. https://doi.org/10.1021/ja512658m
31. Wang X, Kehr G, Daniliuc CG, Erker G (2014) Internal Adduct Formation of Active
Intramolecular C 4 -Bridged Frustrated Phosphane/Borane Lewis Pairs. J Am Chem Soc
136:3293–3303. https://doi.org/10.1021/ja413060u
32. Ye K-Y, Wang X, Daniliuc CG, Kehr G, Erker G (2017) A Ferrocene-Based Phosphane/Borane
Frustrated Lewis Pair for Asymmetric Imine Reduction. Eur J Inorg Chem 368–371. https://
doi.org/10.1002/ejic.201600834
33. Liu X, Liu T, Meng W, Du, H (2018) Asymmetric Hydrogenation of Imines with Chiral AlkeneDerived Boron Lewis Acids. Org Biomol Chem 16:8686–8689. https://doi.org/10.1039/C8O
B02446D
34. Tu X-S, Zeng N-N, Li R-Y, Zhao Y-Q, Xie D-Z, Peng Q, Wang X-C (2018) C 2 -Symmetric
Bicyclic Bisborane Catalysts: Kinetic or Thermodynamic Products of a Reversible Hydroboration of Dienes. Angew Chem Int Ed 57:15096–15100. https://doi.org/10.1002/anie.201
808289
35. Lam J, Günther BAR, Farrell JM, Eisenberger P, Bestvater BP, Newman PD, Melen RL,
Crudden CM, Stephan DW (2016) Chiral Carbene-Borane Adducts: Precursors for Borenium
Catalysts for Asymmetric FLP Hydrogenations. Dalton Trans 45:15303–15316. https://doi.
org/10.1039/C6DT02202B
36. Mercea DM, Howlett MG, Piascik AD, Scott DJ, Steven A, Ashley AE, Fuchter MJ (2019)
Enantioselective Reduction of N-Alkyl Ketimines with Frustrated Lewis Pair Catalysis Using
Chiral Borenium Ions. Chem Commun 55:7077–7080. https://doi.org/10.1039/C9CC02900A