384
F. Holtrop et al.
24. Dong Z, Cramer HH, Schmidtmann M, Paul LA, Siewert I, Müller T (2018) Evidence for
a Single Electron Shift in a Lewis Acid-Base Reaction. J Am Chem Soc 140:15419–15424.
https://doi.org/10.1021/jacs.8b09214
25. Soltani Y, Dasgupta A, Gazis TA, Ould DMC, Richards E, Slater B, Stefkova K, Vladimirov
VY, Wilkins LC, Willcox D, Melen RL (2020) Radical Reactivity of Frustrated Lewis Pairs
with Diaryl Esters. Cell Rep Phys Sci 1:100016. https://doi.org/10.1016/j.xcrp.2020.100016
26. Aramaki Y, Imaizumi N, Hotta M, Kumagai J, Ooi T (2020) Exploiting Single-Electron Transfer
in Lewis Pairs for Catalytic Bond-Forming Reactions. Chem Sci 11:4305–4311. https://doi.
org/10.1039/D0SC01159B
27. Holtrop F, Jupp AR, van Leest NP, Paradiz Dominguez M, Williams RM, Brouwer AM, de
Bruin B, Ehlers AW, Slootweg JC (2020) Photoinduced and Thermal Single-Electron Transfer
to Generate Radicals from Frustrated Lewis Pairs. Chem Eur J 26:9005–9011. https://doi.org/
10.1002/chem.202001494
28. Kwaan RJ, Harlan CJ, Norton JR (2001) Generation and Characterization of the
Tris(pentafluorophenyl)borane Radical Anion. Organometallics 20:3818–3820. https://doi.
org/10.1021/om010272q
29. 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
30. Zheng X, Wang X, Qiu Y, Li Y, Zhou C, Sui Y, Li Y, Ma J, Wang X (2013) One-Electron
Oxidation of an Organic Molecule by B(C 6 F 5 ) 3 ; Isolation and Structures of Stable Non-ParaSubstituted Triarylamine Cation Radical and Bis(triarylamine) Dication Diradicaloid. J Am
Chem Soc 135:14912–14915. https://doi.org/10.1021/ja407318h
31. Ménard G, Hatnean JA, Cowley HJ, Lough AJ, Rawson JM, Stephan DW (2013) C-H Bond
Activation by Radical Ion Pairs Derived from R 3 P/Al(C 6 F 5 ) 3 Frustrated Lewis Pairs and N 2 O.
J Am Chem Soc 135:6446–6449. https://doi.org/10.1021/ja402964h
32. Otten E, Neu RC, Stephan DW (2009) Complexation of Nitrous Oxide by Frustrated Lewis
Pairs. J Am Chem Soc 131:9918–9919. https://doi.org/10.1021/ja904377v
33. Elmer L-M, Kehr G, Daniliuc CG, Siedow M, Eckert H, Tesch M, Studer A, Williams K, Warren
TH, Erker G (2017) The Chemistry of a Non-Interacting Vicinal Frustrated Phosphane/Borane
Lewis Pair. Chem - Eur J 23:6056–6068. https://doi.org/10.1002/chem.201603954
34. de Oliveira M, Wiegand T, Elmer L-M, Sajid M, Kehr G, Erker G, Magon CJ, Eckert H (2015)
Solid-State EPR Strategies for the Structural Characterization of Paramagnetic NO Adducts of
Frustrated Lewis Pairs (FLPs). J Chem Phys 142:124201. https://doi.org/10.1063/1.4916066
35. de Oliveira M, Knitsch R, Sajid M, Stute A, Elmer L-M, Kehr G, Erker G, Magon CJ, Jeschke
G, Eckert H (2016) Aminoxyl Radicals of B/P Frustrated Lewis Pairs: Refinement of the
Spin-Hamiltonian Parameters by Field- and Temperature-Dependent Pulsed EPR Spectroscopy.
PLoS ONE 11:e0157944. https://doi.org/10.1371/journal.pone.0157944
36. Longobardi LE, Liu L, Grimme S, Stephan DW (2016) Stable Borocyclic Radicals via Frustrated Lewis Pair Hydrogenations. J Am Chem Soc 138:2500–2503. https://doi.org/10.1021/
jacs.5b12823
37. Calderazzo F, Forte C, Marchetti F, Pampaloni G, Pieretti L (2004) Reaction of Phenanthrene9,10-dione with Phenanthrene-9,10-diol: Synthesis and Characterization of the First orthoQuinhydrone Derivative. Helv Chim Acta 87:781–789. https://doi.org/10.1002/hlca.200
490076
38. Eaton SS, Ngendahimana T, Eaton GR, Jupp AR, Stephan DW (2018) Electron Paramagnetic
Resonance of a 10B-Containing Heterocyclic Radical. J Magn Reson 290:76–84. https://doi.
org/10.1016/j.jmr.2018.03.007
39. Chen J, Chen EY-X (2016) Unsolvated Al(C 6 F 5 ) 3 : Structural Features and Electronic
Interaction with Ferrocene. Dalton Trans 45:6105–6110. https://doi.org/10.1039/C5DT03
895B
40. Henthorn JT, Agapie T (2014) Dioxygen Reactivity with a Ferrocene-Lewis Acid Pairing:
Reduction to a Boron Peroxide in the Presence of Tris(pentafluorophenyl)borane. Angew Chem
Int Ed 53:12893–12896. https://doi.org/10.1002/anie.201408462
F. Holtrop et al.
24. Dong Z, Cramer HH, Schmidtmann M, Paul LA, Siewert I, Müller T (2018) Evidence for
a Single Electron Shift in a Lewis Acid-Base Reaction. J Am Chem Soc 140:15419–15424.
https://doi.org/10.1021/jacs.8b09214
25. Soltani Y, Dasgupta A, Gazis TA, Ould DMC, Richards E, Slater B, Stefkova K, Vladimirov
VY, Wilkins LC, Willcox D, Melen RL (2020) Radical Reactivity of Frustrated Lewis Pairs
with Diaryl Esters. Cell Rep Phys Sci 1:100016. https://doi.org/10.1016/j.xcrp.2020.100016
26. Aramaki Y, Imaizumi N, Hotta M, Kumagai J, Ooi T (2020) Exploiting Single-Electron Transfer
in Lewis Pairs for Catalytic Bond-Forming Reactions. Chem Sci 11:4305–4311. https://doi.
org/10.1039/D0SC01159B
27. Holtrop F, Jupp AR, van Leest NP, Paradiz Dominguez M, Williams RM, Brouwer AM, de
Bruin B, Ehlers AW, Slootweg JC (2020) Photoinduced and Thermal Single-Electron Transfer
to Generate Radicals from Frustrated Lewis Pairs. Chem Eur J 26:9005–9011. https://doi.org/
10.1002/chem.202001494
28. Kwaan RJ, Harlan CJ, Norton JR (2001) Generation and Characterization of the
Tris(pentafluorophenyl)borane Radical Anion. Organometallics 20:3818–3820. https://doi.
org/10.1021/om010272q
29. 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
30. Zheng X, Wang X, Qiu Y, Li Y, Zhou C, Sui Y, Li Y, Ma J, Wang X (2013) One-Electron
Oxidation of an Organic Molecule by B(C 6 F 5 ) 3 ; Isolation and Structures of Stable Non-ParaSubstituted Triarylamine Cation Radical and Bis(triarylamine) Dication Diradicaloid. J Am
Chem Soc 135:14912–14915. https://doi.org/10.1021/ja407318h
31. Ménard G, Hatnean JA, Cowley HJ, Lough AJ, Rawson JM, Stephan DW (2013) C-H Bond
Activation by Radical Ion Pairs Derived from R 3 P/Al(C 6 F 5 ) 3 Frustrated Lewis Pairs and N 2 O.
J Am Chem Soc 135:6446–6449. https://doi.org/10.1021/ja402964h
32. Otten E, Neu RC, Stephan DW (2009) Complexation of Nitrous Oxide by Frustrated Lewis
Pairs. J Am Chem Soc 131:9918–9919. https://doi.org/10.1021/ja904377v
33. Elmer L-M, Kehr G, Daniliuc CG, Siedow M, Eckert H, Tesch M, Studer A, Williams K, Warren
TH, Erker G (2017) The Chemistry of a Non-Interacting Vicinal Frustrated Phosphane/Borane
Lewis Pair. Chem - Eur J 23:6056–6068. https://doi.org/10.1002/chem.201603954
34. de Oliveira M, Wiegand T, Elmer L-M, Sajid M, Kehr G, Erker G, Magon CJ, Eckert H (2015)
Solid-State EPR Strategies for the Structural Characterization of Paramagnetic NO Adducts of
Frustrated Lewis Pairs (FLPs). J Chem Phys 142:124201. https://doi.org/10.1063/1.4916066
35. de Oliveira M, Knitsch R, Sajid M, Stute A, Elmer L-M, Kehr G, Erker G, Magon CJ, Jeschke
G, Eckert H (2016) Aminoxyl Radicals of B/P Frustrated Lewis Pairs: Refinement of the
Spin-Hamiltonian Parameters by Field- and Temperature-Dependent Pulsed EPR Spectroscopy.
PLoS ONE 11:e0157944. https://doi.org/10.1371/journal.pone.0157944
36. Longobardi LE, Liu L, Grimme S, Stephan DW (2016) Stable Borocyclic Radicals via Frustrated Lewis Pair Hydrogenations. J Am Chem Soc 138:2500–2503. https://doi.org/10.1021/
jacs.5b12823
37. Calderazzo F, Forte C, Marchetti F, Pampaloni G, Pieretti L (2004) Reaction of Phenanthrene9,10-dione with Phenanthrene-9,10-diol: Synthesis and Characterization of the First orthoQuinhydrone Derivative. Helv Chim Acta 87:781–789. https://doi.org/10.1002/hlca.200
490076
38. Eaton SS, Ngendahimana T, Eaton GR, Jupp AR, Stephan DW (2018) Electron Paramagnetic
Resonance of a 10B-Containing Heterocyclic Radical. J Magn Reson 290:76–84. https://doi.
org/10.1016/j.jmr.2018.03.007
39. Chen J, Chen EY-X (2016) Unsolvated Al(C 6 F 5 ) 3 : Structural Features and Electronic
Interaction with Ferrocene. Dalton Trans 45:6105–6110. https://doi.org/10.1039/C5DT03
895B
40. Henthorn JT, Agapie T (2014) Dioxygen Reactivity with a Ferrocene-Lewis Acid Pairing:
Reduction to a Boron Peroxide in the Presence of Tris(pentafluorophenyl)borane. Angew Chem
Int Ed 53:12893–12896. https://doi.org/10.1002/anie.201408462