6 Lewis Acidic Boranes in Frustrated Lewis Pair Chemistry
231
21. Childs RF, Mulholland DL, Nixon A (1982) The Lewis Acid Complexes of α,β-Unsaturated
Carbonyl and Nitrile Compounds. A Nuclear Magnetic Resonance Study. Can J Chem 60:801–
808. https://doi.org/10.1139/v82-117
22. Christe KO, Dixon DA, McLemore D, Wilson WW, Sheehy JA, Boatz JA (2000) On a Quantitative Scale for Lewis Acidity and Recent Progress in Polynitrogen Chemistry. J Fluor Chem
101:151–153. https://doi.org/10.1016/s0022-1139(99)00151-7
23. Mock MT, Potter RG, Camaioni DM, Li J, Dougherty WJ, Kassel WS, Twamley B, DuBois DL
(2009) Thermodynamic Studies and Hydride Transfer Reactions from a Rhodium Complex
to BX 3 Compounds. J Am Chem Soc 131:14454–14465. https://doi.org/10.1021/ja905287q
24. Jupp AR, Johnstone TC, Stephan DW (2018) The Global Electrophilicity Index as a Metric
for Lewis Acidity. Dalton Trans 47:7029–7035. https://doi.org/10.1039/c8dt01699b
25. Massey AG, Park AJ, Stone FGA (1963) Tris(pentafluorophenyl)boron. Proc Chem Soc
212. https://doi.org/10.1039/PS9630000189
26. Carden JL, Dasgupta A, Melen RL (2020) Halogenated Triarylboranes: Synthesis, Properties
and Applications in Catalysis. Chem Soc Rev 49:1706–1725. https://doi.org/10.1039/C9C
S00769E
27. Herrington TJ, Thom AJW, White AJP, Ashley AE (2012) Novel H 2 Activation by a Tris[3,5bis(trifluoromethyl)phenyl]borane Frustrated Lewis Pair. Dalton Trans 41:9019–9022. https://
doi.org/10.1039/c2dt30384a
28. Yin Q, Soltani Y, Melen RL, Oestreich M (2017) BAr F 3 -Catalyzed Imine Hydroboration with
Pinacolborane not Requiring the Assistance of an Additional Lewis Base. Organometallics
36:2381–2384. https://doi.org/10.1021/acs.organomet.7b00381
29. Keess S, Simonneau A, Oestreich M (2015) Direct and Transfer Hydrosilylation Reactions Catalyzed by Fully or Partially Fluorinated Triarylboranes: a Systematic Study.
Organometallics 34:790–799. https://doi.org/10.1021/om501284a
30. Carden JL, Gierlichs L, Wass D, Browne DL, Melen RL (2019) Unlocking the Catalytic
Potential of Tris(3,4,5-trifluorophenyl)borane with Microwave Irradiation. Chem Commun
55:318–321. https://doi.org/10.1039/c8cc09459d
31. Yin Q, Kemper S, Klare HFT, Oestreich M (2016) Boron Lewis Acid-Catalyzed Hydroboration of Alkenes with Pinacolborane: BAr F 3 Does What B(C 6 F 5 ) 3 Cannot Do! Chem Eur J
22:13840–13844. https://doi.org/10.1002/chem.201603466
32. Naumann D, Butler H, Gnann R (1992) Darstellung und Eigenschaften neuer
Tris(fluoraryl)borane. Z Anorg Allg Chem 618:74–76. https://doi.org/10.1002/zaac.199261
80113
33. Cornet SM, Dillon KB, Entwistle CD, Fox MA, Goeta AE, Goodwin HP, Marder TB,
Thompson AL (2003) Synthesis and Characterisation of Some New Boron Compounds
Containing the 2,4,6-(CF 3 ) 3 C 6 H 2 (fluoromes = Ar), 2,6-(CF 3 ) 2 C 6 H 3 (fluoroxyl = Ar ), or
2,4-(CF 3 ) 2 C 6 H 3 (Ar ) Ligands. Dalton Trans 4395–4405. https://doi.org/10.1039/b309820f
34. Blagg RJ, Lawrence EJ, Resner K, Oganesyan VS, Herrington TJ, Ashley AE, Wildgoose GG (2016) Exploring Structural and Electronic Effects in Three Isomers of
Tris{bis(trifluoromethyl)phenyl}borane: Towards the Combined Electrochemical-Frustrated
Lewis Pair Activation of H 2 . Dalton Trans 45:6023–6031. https://doi.org/10.1039/c5dt01
918d
35. Toyota S, Asakura M, Oki M, Toda F (2000) Structural and Stereochemical Studies of Tris[2(trifluoromethyl)phenyl]borane: Spontaneous Resolution, Stereodynamics, and Intramolecular C-F···B Interactions. Bull Chem Soc Jpn 73:2357–2362. https://doi.org/10.1246/bcsj.73.
2357
36. Li L, Marks TJ (1998) New Organo-Lewis Acids. Tris(β-perfluoronaphthyl)borane (PNB) as a
Highly Active Cocatalyst for Metallocene-Mediated Ziegler−Natta α-Olefin Polymerization.
Organometallics 17:3996–4003. https://doi.org/10.1021/om980229b
37. Chen YX, Metz MV, Li L, Stern CL, Marks TJ (1998) Sterically Encumbered (Perfluoroaryl)borane and Aluminate Cocatalysts for Tuning Cation−Anion Ion Pair Structure
and Reactivity in Metallocene Polymerization Processes. A Synthetic, Structural, and
Polymerization Study. J Am Chem Soc 120:6287–6305. https://doi.org/10.1021/ja973769t
231
21. Childs RF, Mulholland DL, Nixon A (1982) The Lewis Acid Complexes of α,β-Unsaturated
Carbonyl and Nitrile Compounds. A Nuclear Magnetic Resonance Study. Can J Chem 60:801–
808. https://doi.org/10.1139/v82-117
22. Christe KO, Dixon DA, McLemore D, Wilson WW, Sheehy JA, Boatz JA (2000) On a Quantitative Scale for Lewis Acidity and Recent Progress in Polynitrogen Chemistry. J Fluor Chem
101:151–153. https://doi.org/10.1016/s0022-1139(99)00151-7
23. Mock MT, Potter RG, Camaioni DM, Li J, Dougherty WJ, Kassel WS, Twamley B, DuBois DL
(2009) Thermodynamic Studies and Hydride Transfer Reactions from a Rhodium Complex
to BX 3 Compounds. J Am Chem Soc 131:14454–14465. https://doi.org/10.1021/ja905287q
24. Jupp AR, Johnstone TC, Stephan DW (2018) The Global Electrophilicity Index as a Metric
for Lewis Acidity. Dalton Trans 47:7029–7035. https://doi.org/10.1039/c8dt01699b
25. Massey AG, Park AJ, Stone FGA (1963) Tris(pentafluorophenyl)boron. Proc Chem Soc
212. https://doi.org/10.1039/PS9630000189
26. Carden JL, Dasgupta A, Melen RL (2020) Halogenated Triarylboranes: Synthesis, Properties
and Applications in Catalysis. Chem Soc Rev 49:1706–1725. https://doi.org/10.1039/C9C
S00769E
27. Herrington TJ, Thom AJW, White AJP, Ashley AE (2012) Novel H 2 Activation by a Tris[3,5bis(trifluoromethyl)phenyl]borane Frustrated Lewis Pair. Dalton Trans 41:9019–9022. https://
doi.org/10.1039/c2dt30384a
28. Yin Q, Soltani Y, Melen RL, Oestreich M (2017) BAr F 3 -Catalyzed Imine Hydroboration with
Pinacolborane not Requiring the Assistance of an Additional Lewis Base. Organometallics
36:2381–2384. https://doi.org/10.1021/acs.organomet.7b00381
29. Keess S, Simonneau A, Oestreich M (2015) Direct and Transfer Hydrosilylation Reactions Catalyzed by Fully or Partially Fluorinated Triarylboranes: a Systematic Study.
Organometallics 34:790–799. https://doi.org/10.1021/om501284a
30. Carden JL, Gierlichs L, Wass D, Browne DL, Melen RL (2019) Unlocking the Catalytic
Potential of Tris(3,4,5-trifluorophenyl)borane with Microwave Irradiation. Chem Commun
55:318–321. https://doi.org/10.1039/c8cc09459d
31. Yin Q, Kemper S, Klare HFT, Oestreich M (2016) Boron Lewis Acid-Catalyzed Hydroboration of Alkenes with Pinacolborane: BAr F 3 Does What B(C 6 F 5 ) 3 Cannot Do! Chem Eur J
22:13840–13844. https://doi.org/10.1002/chem.201603466
32. Naumann D, Butler H, Gnann R (1992) Darstellung und Eigenschaften neuer
Tris(fluoraryl)borane. Z Anorg Allg Chem 618:74–76. https://doi.org/10.1002/zaac.199261
80113
33. Cornet SM, Dillon KB, Entwistle CD, Fox MA, Goeta AE, Goodwin HP, Marder TB,
Thompson AL (2003) Synthesis and Characterisation of Some New Boron Compounds
Containing the 2,4,6-(CF 3 ) 3 C 6 H 2 (fluoromes = Ar), 2,6-(CF 3 ) 2 C 6 H 3 (fluoroxyl = Ar ), or
2,4-(CF 3 ) 2 C 6 H 3 (Ar ) Ligands. Dalton Trans 4395–4405. https://doi.org/10.1039/b309820f
34. Blagg RJ, Lawrence EJ, Resner K, Oganesyan VS, Herrington TJ, Ashley AE, Wildgoose GG (2016) Exploring Structural and Electronic Effects in Three Isomers of
Tris{bis(trifluoromethyl)phenyl}borane: Towards the Combined Electrochemical-Frustrated
Lewis Pair Activation of H 2 . Dalton Trans 45:6023–6031. https://doi.org/10.1039/c5dt01
918d
35. Toyota S, Asakura M, Oki M, Toda F (2000) Structural and Stereochemical Studies of Tris[2(trifluoromethyl)phenyl]borane: Spontaneous Resolution, Stereodynamics, and Intramolecular C-F···B Interactions. Bull Chem Soc Jpn 73:2357–2362. https://doi.org/10.1246/bcsj.73.
2357
36. Li L, Marks TJ (1998) New Organo-Lewis Acids. Tris(β-perfluoronaphthyl)borane (PNB) as a
Highly Active Cocatalyst for Metallocene-Mediated Ziegler−Natta α-Olefin Polymerization.
Organometallics 17:3996–4003. https://doi.org/10.1021/om980229b
37. Chen YX, Metz MV, Li L, Stern CL, Marks TJ (1998) Sterically Encumbered (Perfluoroaryl)borane and Aluminate Cocatalysts for Tuning Cation−Anion Ion Pair Structure
and Reactivity in Metallocene Polymerization Processes. A Synthetic, Structural, and
Polymerization Study. J Am Chem Soc 120:6287–6305. https://doi.org/10.1021/ja973769t