6 Lewis Acidic Boranes in Frustrated Lewis Pair Chemistry
233
55. Li H, Aquino AJA, Cordes DB, Hung-Low F, Hase WL, Krempner C (2013) A Zwitterionic
Carbanion Frustrated by Boranes – Dihydrogen Cleavage with Weak Lewis Acids Via an
“Inverse” Frustrated Lewis Pair Approach. J Am Chem Soc 135:16066–16069. https://doi.
org/10.1021/ja409330h
56. Mummadi S, Unruh DK, Zhao J, Li S, Krempner C (2016) “Inverse” Frustrated Lewis Pairs
– Activation of Dihydrogen with Organosuperbases and Moderate to Weak Lewis Acids. J
Am Chem Soc 138:3286–3289. https://doi.org/10.1021/jacs.5b13545
57. Mummadi S, Brar A, Wang G, Kenefake D, Diaz R, Unruh DK, Li S, Krempner (2018)
“Inverse” Frustrated Lewis Pairs: an Inverse FLP Approach to the Catalytic Metal Free
Hydrogenation of Ketones. Chem Eur J 24:16526–16531. https://doi.org/10.1002/chem.201
804370
58. Heiden ZM, Lathem AP (2015) Establishing the Hydride Donor Abilities of Main Group
Hydrides. Organometallics 34:1818–1827. https://doi.org/10.1021/om5011512
59. Ilic S, Alherz A, Musgrave CB, Glusac KD (2018) Thermodynamic and Kinetic Hydricities
of Metal-Free Hydrides. Chem Soc Rev 47:2809–2836. https://doi.org/10.1039/c7cs00171a
60. Golub IE, Filippov OA, Belkova NV, Epstein L, Shubina E (2018) Changing the Boron
Environment – a Powerful Tool to Tune the Reactivity. Sci Trends. https://doi.org/10.31988/
scitrends.20968
61. Bergquist C, Bridgewater BM, Harlan CJ, Norton JR, Friesner RA, Parkin G (2000) Aqua,
Alcohol, and Acetonitrile Adducts of Tris(perfluorophenyl)borane: Evaluation of Brønsted
Acidity and Ligand Lability with Experimental and Computational Methods. J Am Chem Soc
122:10581–10590. https://doi.org/10.1021/ja001915g
62. Di Saverio A, Focante F, Camurati I, Resconi L, Beringhelli T, D’Alfonso G, Donghi
D, Maggioni D, Mercandelli P, Sironi A (2005) Oxygen-Bridged Borate Anions from
Tris(pentafluorophenyl)borane: Synthesis, NMR Characterization, and Reactivity. Inorg
Chem 44:5030–5041. https://doi.org/10.1021/ic0502168
63. Lathem AP, Heiden ZM (2017) Quantification of Lewis Acid Induced Brønsted Acidity of
Protogenic Lewis Bases. Dalton Trans 46:5976–5985. https://doi.org/10.1039/c7dt00777a
64. Fasano V, Ingleson MJ (2018) Recent Advances in Water-Tolerance in Frustrated Lewis Pair
Chemistry. Synthesis 50:1783–1795. https://doi.org/10.1055/s-0037-1609843
65. Lindqvist M, Sarnela N, Sumerin V, Chernichenko K, Leskelä M, Repo T (2012) Heterolytic
Dihydrogen Activation by B(C 6 F 5 ) 3 and Carbonyl Compounds. Dalton Trans 41:4310–4312.
https://doi.org/10.1039/c2dt12268e
66. Longobardi LE, Tang C, Stephan DW (2014) Stoichiometric Reductions of Alkyl-Substituted
Ketones and Aldehydes to Borinic Esters. Dalton Trans. 43:15723–15726. https://doi.org/10.
1039/c4dt02648a
67. Mahdi T, Stephan DW (2014) Enabling Catalytic Ketone Hydrogenation by Frustrated Lewis
Pairs. J Am Chem Soc 136:15809–15812. https://doi.org/10.1021/ja508829x
68. Scott DJ, Fuchter MJ, Ashley AE (2014) Nonmetal Catalyzed Hydrogenation of Carbonyl
Compounds. J Am Chem Soc 136:15813–15816. https://doi.org/10.1021/ja5088979
69. Mahdi T, Stephan DW (2015) Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes. Angew Chem Int Ed
54:8511–8514. https://doi.org/10.1002/anie.201503087
70. Hounjet LJ, Bannwarth C, Garon CN, Caputo CB, Grimme S, Stephan DW (2013) Combinations of Ethers and B(C 6 F 5 ) 3 Function as Hydrogenation Catalysts. Angew Chem Int Ed
52:7492–7495. https://doi.org/10.1002/anie.201303166
71. Morris RH (2016) Brønsted–Lowry Acid Strength of Metal Hydride and Dihydrogen
Complexes. Chem Rev 116:8588–8654. https://doi.org/10.1021/acs.chemrev.5b00695
72. Scott DJ, Simmons TR, Lawrence EJ, Wildgoose GG, Fuchter MJ, Ashley AE (2015) Facile
Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation. ACS Catal
5:5540–5544. https://doi.org/10.1021/acscatal.5b01417
73. Ghattas G, Bizzarri C, Hölscher M, Langanke J, Gürtler C, Leitner W, Subhani MA (2017)
Interaction of Formaldehyde With a Water-Tolerant Frustrated Lewis Pair. Chem Commun
53:3205–3208. https://doi.org/10.1039/c6cc08044h
233
55. Li H, Aquino AJA, Cordes DB, Hung-Low F, Hase WL, Krempner C (2013) A Zwitterionic
Carbanion Frustrated by Boranes – Dihydrogen Cleavage with Weak Lewis Acids Via an
“Inverse” Frustrated Lewis Pair Approach. J Am Chem Soc 135:16066–16069. https://doi.
org/10.1021/ja409330h
56. Mummadi S, Unruh DK, Zhao J, Li S, Krempner C (2016) “Inverse” Frustrated Lewis Pairs
– Activation of Dihydrogen with Organosuperbases and Moderate to Weak Lewis Acids. J
Am Chem Soc 138:3286–3289. https://doi.org/10.1021/jacs.5b13545
57. Mummadi S, Brar A, Wang G, Kenefake D, Diaz R, Unruh DK, Li S, Krempner (2018)
“Inverse” Frustrated Lewis Pairs: an Inverse FLP Approach to the Catalytic Metal Free
Hydrogenation of Ketones. Chem Eur J 24:16526–16531. https://doi.org/10.1002/chem.201
804370
58. Heiden ZM, Lathem AP (2015) Establishing the Hydride Donor Abilities of Main Group
Hydrides. Organometallics 34:1818–1827. https://doi.org/10.1021/om5011512
59. Ilic S, Alherz A, Musgrave CB, Glusac KD (2018) Thermodynamic and Kinetic Hydricities
of Metal-Free Hydrides. Chem Soc Rev 47:2809–2836. https://doi.org/10.1039/c7cs00171a
60. Golub IE, Filippov OA, Belkova NV, Epstein L, Shubina E (2018) Changing the Boron
Environment – a Powerful Tool to Tune the Reactivity. Sci Trends. https://doi.org/10.31988/
scitrends.20968
61. Bergquist C, Bridgewater BM, Harlan CJ, Norton JR, Friesner RA, Parkin G (2000) Aqua,
Alcohol, and Acetonitrile Adducts of Tris(perfluorophenyl)borane: Evaluation of Brønsted
Acidity and Ligand Lability with Experimental and Computational Methods. J Am Chem Soc
122:10581–10590. https://doi.org/10.1021/ja001915g
62. Di Saverio A, Focante F, Camurati I, Resconi L, Beringhelli T, D’Alfonso G, Donghi
D, Maggioni D, Mercandelli P, Sironi A (2005) Oxygen-Bridged Borate Anions from
Tris(pentafluorophenyl)borane: Synthesis, NMR Characterization, and Reactivity. Inorg
Chem 44:5030–5041. https://doi.org/10.1021/ic0502168
63. Lathem AP, Heiden ZM (2017) Quantification of Lewis Acid Induced Brønsted Acidity of
Protogenic Lewis Bases. Dalton Trans 46:5976–5985. https://doi.org/10.1039/c7dt00777a
64. Fasano V, Ingleson MJ (2018) Recent Advances in Water-Tolerance in Frustrated Lewis Pair
Chemistry. Synthesis 50:1783–1795. https://doi.org/10.1055/s-0037-1609843
65. Lindqvist M, Sarnela N, Sumerin V, Chernichenko K, Leskelä M, Repo T (2012) Heterolytic
Dihydrogen Activation by B(C 6 F 5 ) 3 and Carbonyl Compounds. Dalton Trans 41:4310–4312.
https://doi.org/10.1039/c2dt12268e
66. Longobardi LE, Tang C, Stephan DW (2014) Stoichiometric Reductions of Alkyl-Substituted
Ketones and Aldehydes to Borinic Esters. Dalton Trans. 43:15723–15726. https://doi.org/10.
1039/c4dt02648a
67. Mahdi T, Stephan DW (2014) Enabling Catalytic Ketone Hydrogenation by Frustrated Lewis
Pairs. J Am Chem Soc 136:15809–15812. https://doi.org/10.1021/ja508829x
68. Scott DJ, Fuchter MJ, Ashley AE (2014) Nonmetal Catalyzed Hydrogenation of Carbonyl
Compounds. J Am Chem Soc 136:15813–15816. https://doi.org/10.1021/ja5088979
69. Mahdi T, Stephan DW (2015) Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes. Angew Chem Int Ed
54:8511–8514. https://doi.org/10.1002/anie.201503087
70. Hounjet LJ, Bannwarth C, Garon CN, Caputo CB, Grimme S, Stephan DW (2013) Combinations of Ethers and B(C 6 F 5 ) 3 Function as Hydrogenation Catalysts. Angew Chem Int Ed
52:7492–7495. https://doi.org/10.1002/anie.201303166
71. Morris RH (2016) Brønsted–Lowry Acid Strength of Metal Hydride and Dihydrogen
Complexes. Chem Rev 116:8588–8654. https://doi.org/10.1021/acs.chemrev.5b00695
72. Scott DJ, Simmons TR, Lawrence EJ, Wildgoose GG, Fuchter MJ, Ashley AE (2015) Facile
Protocol for Water-Tolerant “Frustrated Lewis Pair”-Catalyzed Hydrogenation. ACS Catal
5:5540–5544. https://doi.org/10.1021/acscatal.5b01417
73. Ghattas G, Bizzarri C, Hölscher M, Langanke J, Gürtler C, Leitner W, Subhani MA (2017)
Interaction of Formaldehyde With a Water-Tolerant Frustrated Lewis Pair. Chem Commun
53:3205–3208. https://doi.org/10.1039/c6cc08044h