232
T. A. Gazis et al.
38. Ullrich M, Lough AJ, Stephan DW (2009) Reversible, Metal-Free, Heterolytic Activation of
H 2 at Room Temperature. J Am Chem Soc 131:52–53. https://doi.org/10.1021/ja808506t
39. Wada M, Kanzaki M, Ogura H, Hayase S, Erabi T (1995) Tris(2-6-dimethoxephenyl)borane
and its Adducts. J Organomet Chem 485:127–133. https://doi.org/10.1016/0022-328x(94)247
63-9
40. Leffler JE, Watts GB, Tanigaki T, Dolan E, Miller DS (1970) Triarylboron Anion Radicals
and the Reductive Cleavage of Boron Compounds. J Am Chem Soc 92:6825–6830. https://
doi.org/10.1021/ja00726a018
41. Dorkó É, 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
42. Ashley AE, Herrington TJ, Wildgoose GG, Zaher H, Thompson AL, Rees NH, Krämer T,
O’Hare D (2011) Separating Electrophilicity and Lewis Acidity: The Synthesis, Characterization, and Electrochemistry of the Electron Deficient Tris(aryl)boranes B(C 6 F 5 ) 3–n (C 6 Cl 5 ) n
(n = 1–3). J Am Chem Soc 133:14727–14740. https://doi.org/10.1021/ja205037t
43. Blagg RJ, Simmons TR, Hatton GR, Courtney JM, Bennett EL, Lawrence EJ, Wildgoose GG
(2016) Novel B(Ar ) 2 (Ar ) Hetero-tri(aryl)boranes: a Systematic Study of Lewis Acidity.
Dalton Trans. 45:6032–6043. https://doi.org/10.1039/c5dt03854e
44. 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
45. Körte LA, Schwabedissen J, Soffner M, Blomeyer S, Reuter CG, Vishnevskiy YV, Neumann
B, Stammler HG, Mitzel NW (2017) Tris(perfluorotolyl)borane—a Boron Lewis Superacid.
Angew Chem Int Ed 56:8578–8582. https://doi.org/10.1002/anie.201704097
46. Gyömöre Á, Bakos M, Földes T, Pápai I, Domján A, Soós T (2015) Moisture-Tolerant
Frustrated Lewis Pair Catalyst for Hydrogenation of Aldehydes and Ketones. ACS Catal
5:5366–5372. https://doi.org/10.1021/acscatal.5b01299
47. Dorkó É, Kótai B, Földes T, Gyömöre Á, Pápai I, Soós T (2017) Correlating Electronic and
Catalytic Properties of Frustrated Lewis Pairs for Imine Hydrogenation. J Organomet Chem
847:258–262. https://doi.org/10.1016/j.jorganchem.2017.04.031
48. Blagg RJ, Wildgoose GG (2016) H 2 Activation Using the First 1 : 1 : 1 Hetero-tri(aryl)borane.
RSC Adv 6:42421–42427. https://doi.org/10.1039/c6ra07007h
49. Chai J, Lewis SP, Collins S, Sciarone TJJ, Henderson LD, Chase PA, Irvine GJ, Piers WE,
Elsegood MRJ, Clegg W (2007) Formation of Chelated Counteranions Using Lewis Acidic
Diboranes: Relevance to Isobutene Polymerization. Organometallics 26:5667–5679. https://
doi.org/10.1021/om700672q
50. Wondimagegn T, Xu Z, Vanka K, Ziegler T (2005) Possible Thermal Decomposition
Routes in [MeB(C 6 F 5 ) 3 ] - [L 2 TiMe + ] as Deactivation Pathways in Olefin Polymerization
Catalysis: a Combined Density Functional Theory and Molecular Mechanics Investigation.
Organometallics 24:2076–2085. https://doi.org/10.1021/om049157g
51. Morgan MM, Marwitz AJ, Piers WE, Parvez M (2013) Comparative Lewis Acidity in Fluoroarylboranes: B(o-HC 6 F 4 ) 3 , B(p-HC 6 F 4 ) 3 , and B(C 6 F 5 ) 3 . Organometallics 32:317–322.
https://doi.org/10.1021/om3011195
52. Nicasio JA, Steinberg S, Inés B, Alcarazo M (2013) Tuning the Lewis Acidity of Boranes
in Frustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor
Alkenes. Chem Eur J 19:11016–11020. https://doi.org/10.1002/chem.201301158
53. Khan I, Manzotti M, Tizzard GJ, Coles SJ, Melen RL, Morrill LC (2017) Frustrated Lewis
Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita–Baylis–Hillman Adducts and Sequential
Organo-FLP Catalysis. ACS Catal 7:7748–7752. https://doi.org/10.1021/acscatal.7b03077
54. Santi M, Ould DMC, Wenz J, Soltani Y, Melen RL, Wirth T (2019) Metal-Free Tandem
Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones. Angew
Chem Int Ed 58:7861–7865. https://doi.org/10.1002/anie.201902985
T. A. Gazis et al.
38. Ullrich M, Lough AJ, Stephan DW (2009) Reversible, Metal-Free, Heterolytic Activation of
H 2 at Room Temperature. J Am Chem Soc 131:52–53. https://doi.org/10.1021/ja808506t
39. Wada M, Kanzaki M, Ogura H, Hayase S, Erabi T (1995) Tris(2-6-dimethoxephenyl)borane
and its Adducts. J Organomet Chem 485:127–133. https://doi.org/10.1016/0022-328x(94)247
63-9
40. Leffler JE, Watts GB, Tanigaki T, Dolan E, Miller DS (1970) Triarylboron Anion Radicals
and the Reductive Cleavage of Boron Compounds. J Am Chem Soc 92:6825–6830. https://
doi.org/10.1021/ja00726a018
41. Dorkó É, 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
42. Ashley AE, Herrington TJ, Wildgoose GG, Zaher H, Thompson AL, Rees NH, Krämer T,
O’Hare D (2011) Separating Electrophilicity and Lewis Acidity: The Synthesis, Characterization, and Electrochemistry of the Electron Deficient Tris(aryl)boranes B(C 6 F 5 ) 3–n (C 6 Cl 5 ) n
(n = 1–3). J Am Chem Soc 133:14727–14740. https://doi.org/10.1021/ja205037t
43. Blagg RJ, Simmons TR, Hatton GR, Courtney JM, Bennett EL, Lawrence EJ, Wildgoose GG
(2016) Novel B(Ar ) 2 (Ar ) Hetero-tri(aryl)boranes: a Systematic Study of Lewis Acidity.
Dalton Trans. 45:6032–6043. https://doi.org/10.1039/c5dt03854e
44. 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
45. Körte LA, Schwabedissen J, Soffner M, Blomeyer S, Reuter CG, Vishnevskiy YV, Neumann
B, Stammler HG, Mitzel NW (2017) Tris(perfluorotolyl)borane—a Boron Lewis Superacid.
Angew Chem Int Ed 56:8578–8582. https://doi.org/10.1002/anie.201704097
46. Gyömöre Á, Bakos M, Földes T, Pápai I, Domján A, Soós T (2015) Moisture-Tolerant
Frustrated Lewis Pair Catalyst for Hydrogenation of Aldehydes and Ketones. ACS Catal
5:5366–5372. https://doi.org/10.1021/acscatal.5b01299
47. Dorkó É, Kótai B, Földes T, Gyömöre Á, Pápai I, Soós T (2017) Correlating Electronic and
Catalytic Properties of Frustrated Lewis Pairs for Imine Hydrogenation. J Organomet Chem
847:258–262. https://doi.org/10.1016/j.jorganchem.2017.04.031
48. Blagg RJ, Wildgoose GG (2016) H 2 Activation Using the First 1 : 1 : 1 Hetero-tri(aryl)borane.
RSC Adv 6:42421–42427. https://doi.org/10.1039/c6ra07007h
49. Chai J, Lewis SP, Collins S, Sciarone TJJ, Henderson LD, Chase PA, Irvine GJ, Piers WE,
Elsegood MRJ, Clegg W (2007) Formation of Chelated Counteranions Using Lewis Acidic
Diboranes: Relevance to Isobutene Polymerization. Organometallics 26:5667–5679. https://
doi.org/10.1021/om700672q
50. Wondimagegn T, Xu Z, Vanka K, Ziegler T (2005) Possible Thermal Decomposition
Routes in [MeB(C 6 F 5 ) 3 ] - [L 2 TiMe + ] as Deactivation Pathways in Olefin Polymerization
Catalysis: a Combined Density Functional Theory and Molecular Mechanics Investigation.
Organometallics 24:2076–2085. https://doi.org/10.1021/om049157g
51. Morgan MM, Marwitz AJ, Piers WE, Parvez M (2013) Comparative Lewis Acidity in Fluoroarylboranes: B(o-HC 6 F 4 ) 3 , B(p-HC 6 F 4 ) 3 , and B(C 6 F 5 ) 3 . Organometallics 32:317–322.
https://doi.org/10.1021/om3011195
52. Nicasio JA, Steinberg S, Inés B, Alcarazo M (2013) Tuning the Lewis Acidity of Boranes
in Frustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor
Alkenes. Chem Eur J 19:11016–11020. https://doi.org/10.1002/chem.201301158
53. Khan I, Manzotti M, Tizzard GJ, Coles SJ, Melen RL, Morrill LC (2017) Frustrated Lewis
Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita–Baylis–Hillman Adducts and Sequential
Organo-FLP Catalysis. ACS Catal 7:7748–7752. https://doi.org/10.1021/acscatal.7b03077
54. Santi M, Ould DMC, Wenz J, Soltani Y, Melen RL, Wirth T (2019) Metal-Free Tandem
Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones. Angew
Chem Int Ed 58:7861–7865. https://doi.org/10.1002/anie.201902985