5 Mechanistic Insight into the Hydrogen Activation by Frustrated Lewis Pairs
207
67. Heshmat M, Privalov T (2017) Computational Elucidation of a Role That Brønsted Acidification of the Lewis Acid-Bound Water Might Play in the Hydrogenation of Carbonyl Compounds
with H 2 in Lewis Basic Solvents. Chem Eur J 23:11489–21149. https://doi.org/10.1002/chem.
201700937
68. Heshmat M, Privalov T (2017) Theory-Based Extension of the Catalyst-Scope in the
Base-Catalyzed Hydrogenation of Ketones: RCOOH-Catalyzed Hydrogenation of Carbonyl
Compounds with H 2 Involving a Proton-Shuttle. Chem Eur J 23:18193-18202. https://doi.
org/10.1002/chem.201702149
69. 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
70. 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
71. Eros 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
72. 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
73. Ghattas G, Bizzarri C, Hölscher M, Langanke J, Gürtler C, Leitner W, Afzal Subhani M (2017)
Interaction of Formaldehyde with a Water-Tolerant Frustrated Lewis Pair. Chem Commun
53:3205–3208. https://doi.org/10.1039/C6CC08044H
74. Scott DJ, Phillips NA, Sapsford JS, Deacy AC, Fuchter MJ, Ashley AE (2016) Versatile
Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid. Angew Chem Int Ed 55:14738–
14742. https://doi.org/10.1002/anie.201606639
75. Fasano V, Ingleson MJ (2017) Expanding Water/Base Tolerant Frustrated Lewis Pair
Chemistry to Alkylamines Enables Broad Scope Reductive Aminations. Chem Eur J
23:2217–2224. https://doi.org/10.1002/chem.201605466
76. Fasano V, Ingelson MJ (2018) Recent Advances in Water-Tolerance in Frustrated Lewis Pair
Chemistry. Synthesis 50:1783–1795. https://doi.org/10.1055/s-0037-1609843
77. Bakos M, Gyömöre A, 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
78. Dorkó E, Szabó M, Kótai B, Pápai I, Domján A, Soós T (2017) Expanding the Boundaries of
Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid
Enables the Reductive Amination of Carbonyls. Angew Chem Int Ed 56:9512–9516. https://
doi.org/10.1002/anie.201703591
79. 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
80. 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
81. Sorochkina K, Chernichenko K, Nieger M, Leskelä M, Repo T (2017) (Dicyclohexyl(2(dimesitylboryl)phenyl)phosphine: En Route to Stable Frustrated Lewis Pairs-Hydrogen
Adducts in Water. Z Naturforsch 72:903–908. https://doi.org/10.1515/znb-2017-0133
82. Heshmat M, Privalov T (2018) Water and a Borohydride/Hydronium Intermediate in
the Borane-Catalyzed Hydrogenation of Carbonyl Compounds with H 2 in Wet Ether: A
Computational Study. J Phys Chem B 122:8952–8962. https://doi.org/10.1021/acs.jpcb.8b0
7506
83. Pu M, Privalov T (2014) Ab Initio Molecular Dynamics Study of Hydrogen Cleavage by a
Lewis Base [tBu 3 P] and a Lewis Acid [B(C 6 F 5 ) 3 ] at the Mesoscopic Level - Dynamics in
the Solute-Solvent Molecular Clusters. Chem Phys Chem 15: 3714–3719. https://doi.org/10.
1002/cphc.201402519
207
67. Heshmat M, Privalov T (2017) Computational Elucidation of a Role That Brønsted Acidification of the Lewis Acid-Bound Water Might Play in the Hydrogenation of Carbonyl Compounds
with H 2 in Lewis Basic Solvents. Chem Eur J 23:11489–21149. https://doi.org/10.1002/chem.
201700937
68. Heshmat M, Privalov T (2017) Theory-Based Extension of the Catalyst-Scope in the
Base-Catalyzed Hydrogenation of Ketones: RCOOH-Catalyzed Hydrogenation of Carbonyl
Compounds with H 2 Involving a Proton-Shuttle. Chem Eur J 23:18193-18202. https://doi.
org/10.1002/chem.201702149
69. 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
70. 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
71. Eros 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
72. 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
73. Ghattas G, Bizzarri C, Hölscher M, Langanke J, Gürtler C, Leitner W, Afzal Subhani M (2017)
Interaction of Formaldehyde with a Water-Tolerant Frustrated Lewis Pair. Chem Commun
53:3205–3208. https://doi.org/10.1039/C6CC08044H
74. Scott DJ, Phillips NA, Sapsford JS, Deacy AC, Fuchter MJ, Ashley AE (2016) Versatile
Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid. Angew Chem Int Ed 55:14738–
14742. https://doi.org/10.1002/anie.201606639
75. Fasano V, Ingleson MJ (2017) Expanding Water/Base Tolerant Frustrated Lewis Pair
Chemistry to Alkylamines Enables Broad Scope Reductive Aminations. Chem Eur J
23:2217–2224. https://doi.org/10.1002/chem.201605466
76. Fasano V, Ingelson MJ (2018) Recent Advances in Water-Tolerance in Frustrated Lewis Pair
Chemistry. Synthesis 50:1783–1795. https://doi.org/10.1055/s-0037-1609843
77. Bakos M, Gyömöre A, 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
78. Dorkó E, Szabó M, Kótai B, Pápai I, Domján A, Soós T (2017) Expanding the Boundaries of
Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid
Enables the Reductive Amination of Carbonyls. Angew Chem Int Ed 56:9512–9516. https://
doi.org/10.1002/anie.201703591
79. 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
80. 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
81. Sorochkina K, Chernichenko K, Nieger M, Leskelä M, Repo T (2017) (Dicyclohexyl(2(dimesitylboryl)phenyl)phosphine: En Route to Stable Frustrated Lewis Pairs-Hydrogen
Adducts in Water. Z Naturforsch 72:903–908. https://doi.org/10.1515/znb-2017-0133
82. Heshmat M, Privalov T (2018) Water and a Borohydride/Hydronium Intermediate in
the Borane-Catalyzed Hydrogenation of Carbonyl Compounds with H 2 in Wet Ether: A
Computational Study. J Phys Chem B 122:8952–8962. https://doi.org/10.1021/acs.jpcb.8b0
7506
83. Pu M, Privalov T (2014) Ab Initio Molecular Dynamics Study of Hydrogen Cleavage by a
Lewis Base [tBu 3 P] and a Lewis Acid [B(C 6 F 5 ) 3 ] at the Mesoscopic Level - Dynamics in
the Solute-Solvent Molecular Clusters. Chem Phys Chem 15: 3714–3719. https://doi.org/10.
1002/cphc.201402519