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T. A. Gazis et al.
74. Thomson JW, Hatnean JA, Hastie JJ, Pasternak A, Stephan DW, Chase PA (2013) Improving
the Industrial Feasibility of Metal-Free Hydrogenation Catalysts Using Chemical Scavengers.
Org Process Res Dev 17:1287–1292. https://doi.org/10.1021/op4000847
75. Fasano V, Radcliffe JE, Ingleson MJ (2016) B(C 6 F 5 ) 3 -Catalyzed Reductive Amination Using
Hydrosilanes. ACS Catal 6:1793–1798. https://doi.org/10.1021/acscatal.5b02896
76. Chen QA, Klare HFT, Oestreich M (2016) Brønsted Acid-Promoted Formation of Stabilized
Silylium Ions for Catalytic Friedel–Crafts C–H Silylation. J Am Chem Soc 138:7868–7871.
https://doi.org/10.1021/jacs.6b04878
77. Pan Y, Chen C, Xu X, Zhao H, Han J, Li H, Xu L, Fan Q, Xiao J (2018) Metal-Free Tandem
Cyclization/Hydrosilylation to Construct Tetrahydroquinoxalines. Green Chem 20:403–411.
https://doi.org/10.1039/c7gc03095a
78. Tiddens MR, Klein Gebbink RJM, Otte M (2016) The B(C 6 F 5 ) 3 -Catalyzed Tandem Meinwald
Rearrangement–Reductive Amination. Org Lett 18:3714–3717. https://doi.org/10.1021/acs.
orglett.6b01744
79. Wilkins LC, Howard JL, Burger S, Frentzel-Beyme L, Browne DL, Melen RL
(2017) Exploring Multistep Continuous-Flow Hydrosilylation Reactions Catalyzed by
Tris(pentafluorophenyl)borane. Adv Synth Catal 359:2580–2584. https://doi.org/10.1002/
adsc.201700349
80. Er˝ os 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 Int Ed 49:6559–6563. https://doi.org/10.1002/anie.201001518
81. Er˝ os G, Nagy K, Mehdi H, Pápai I, Nagy P, Király P, Tárkányi G, Soós T (2012) Catalytic
Hydrogenation with Frustrated Lewis Pairs: Selectivity Achieved by Size-Exclusion Design
of Lewis Acids. Chem Eur J 18:574–585. https://doi.org/10.1002/chem.201102438
82. Bakos M, Gyömöre Á, Domján A, Soós T (2017) Auto-Tandem Catalysis with Frustrated
Lewis Pairs for Reductive Etherification of Aldehydes and Ketones. Angew Chem Int Ed
56:5217–5221. https://doi.org/10.1002/anie.201700231
83. Zhao H, Reibenspies JH, Gabbaï FP (2013) Lewis Acidic Behavior of B(C 6 Cl 5 ) 3 . Dalton
Trans 42:608–610. https://doi.org/10.1039/c2dt31482g
84. Scott DJ, Fuchter MJ, Ashley AE (2014) Metal-Free Hydrogenation Catalyzed by an AirStable Borane: Use of Solvent as a Frustrated Lewis Base. Angew Chem Int Ed 53:10218–
10222. https://doi.org/10.1002/anie.201405531
85. Paradies J (2017) Chiral Borane-Based Lewis Acids for Metal Free Hydrogenations. In Chiral
Lewis Acids, Top Organomet Chem 193–216. https://doi.org/10.1007/3418_2016_173
86. Greb L, Paradies J (2013) Paracyclophane Derivatives in Frustrated Lewis Pair Chemistry.
Top Curr Chem 334:81–100. https://doi.org/10.1007/128_2012_375
87. 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
88. 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
89. Parks DJ, von H. Spence R, Piers WE (1995) Bis(pentafluorophenyl)borane: Synthesis, Properties, and Hydroboration Chemistry of a Highly Electrophilic Borane Reagent. Angew Chem
Int Ed 34:809–811. https://doi.org/10.1002/anie.199508091
90. Axenov KV, Mömming CM, Kehr G, Fröhlich R, Erker G (2010) Structure and Dynamic
Features of an Intramolecular Frustrated Lewis Pair. Chem Eur J 16:14069–14073. https://
doi.org/10.1002/chem.201001814
91. Schwendemann S, Fröhlich R, Kehr G, Erker G (2011) Intramolecular Frustrated N/B Lewis
Pairs by Enamine Hydroboration. Chem Sci 2:1842–1849. https://doi.org/10.1039/c1sc00
124h
92. 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
T. A. Gazis et al.
74. Thomson JW, Hatnean JA, Hastie JJ, Pasternak A, Stephan DW, Chase PA (2013) Improving
the Industrial Feasibility of Metal-Free Hydrogenation Catalysts Using Chemical Scavengers.
Org Process Res Dev 17:1287–1292. https://doi.org/10.1021/op4000847
75. Fasano V, Radcliffe JE, Ingleson MJ (2016) B(C 6 F 5 ) 3 -Catalyzed Reductive Amination Using
Hydrosilanes. ACS Catal 6:1793–1798. https://doi.org/10.1021/acscatal.5b02896
76. Chen QA, Klare HFT, Oestreich M (2016) Brønsted Acid-Promoted Formation of Stabilized
Silylium Ions for Catalytic Friedel–Crafts C–H Silylation. J Am Chem Soc 138:7868–7871.
https://doi.org/10.1021/jacs.6b04878
77. Pan Y, Chen C, Xu X, Zhao H, Han J, Li H, Xu L, Fan Q, Xiao J (2018) Metal-Free Tandem
Cyclization/Hydrosilylation to Construct Tetrahydroquinoxalines. Green Chem 20:403–411.
https://doi.org/10.1039/c7gc03095a
78. Tiddens MR, Klein Gebbink RJM, Otte M (2016) The B(C 6 F 5 ) 3 -Catalyzed Tandem Meinwald
Rearrangement–Reductive Amination. Org Lett 18:3714–3717. https://doi.org/10.1021/acs.
orglett.6b01744
79. Wilkins LC, Howard JL, Burger S, Frentzel-Beyme L, Browne DL, Melen RL
(2017) Exploring Multistep Continuous-Flow Hydrosilylation Reactions Catalyzed by
Tris(pentafluorophenyl)borane. Adv Synth Catal 359:2580–2584. https://doi.org/10.1002/
adsc.201700349
80. Er˝ os 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 Int Ed 49:6559–6563. https://doi.org/10.1002/anie.201001518
81. Er˝ os G, Nagy K, Mehdi H, Pápai I, Nagy P, Király P, Tárkányi G, Soós T (2012) Catalytic
Hydrogenation with Frustrated Lewis Pairs: Selectivity Achieved by Size-Exclusion Design
of Lewis Acids. Chem Eur J 18:574–585. https://doi.org/10.1002/chem.201102438
82. Bakos M, Gyömöre Á, Domján A, Soós T (2017) Auto-Tandem Catalysis with Frustrated
Lewis Pairs for Reductive Etherification of Aldehydes and Ketones. Angew Chem Int Ed
56:5217–5221. https://doi.org/10.1002/anie.201700231
83. Zhao H, Reibenspies JH, Gabbaï FP (2013) Lewis Acidic Behavior of B(C 6 Cl 5 ) 3 . Dalton
Trans 42:608–610. https://doi.org/10.1039/c2dt31482g
84. Scott DJ, Fuchter MJ, Ashley AE (2014) Metal-Free Hydrogenation Catalyzed by an AirStable Borane: Use of Solvent as a Frustrated Lewis Base. Angew Chem Int Ed 53:10218–
10222. https://doi.org/10.1002/anie.201405531
85. Paradies J (2017) Chiral Borane-Based Lewis Acids for Metal Free Hydrogenations. In Chiral
Lewis Acids, Top Organomet Chem 193–216. https://doi.org/10.1007/3418_2016_173
86. Greb L, Paradies J (2013) Paracyclophane Derivatives in Frustrated Lewis Pair Chemistry.
Top Curr Chem 334:81–100. https://doi.org/10.1007/128_2012_375
87. 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
88. 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
89. Parks DJ, von H. Spence R, Piers WE (1995) Bis(pentafluorophenyl)borane: Synthesis, Properties, and Hydroboration Chemistry of a Highly Electrophilic Borane Reagent. Angew Chem
Int Ed 34:809–811. https://doi.org/10.1002/anie.199508091
90. Axenov KV, Mömming CM, Kehr G, Fröhlich R, Erker G (2010) Structure and Dynamic
Features of an Intramolecular Frustrated Lewis Pair. Chem Eur J 16:14069–14073. https://
doi.org/10.1002/chem.201001814
91. Schwendemann S, Fröhlich R, Kehr G, Erker G (2011) Intramolecular Frustrated N/B Lewis
Pairs by Enamine Hydroboration. Chem Sci 2:1842–1849. https://doi.org/10.1039/c1sc00
124h
92. 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