10 Radicals in Frustrated Lewis Pair Chemistry
385
41. Liu LL, Cao LL, Shao Y, Stephan DW (2017) Single Electron Delivery to Lewis Pairs: An
Avenue to Anions by Small Molecule Activation. J Am Chem Soc 139:10062–10071. https://
doi.org/10.1021/jacs.7b05120
42. Holtrop F, Jupp AR, Kooij B, van Leest NP, de Bruin B, Stephan DW, Slootweg JC (2020)
Single-Electron Transfer in Frustrated Lewis Pair Chemistry. Angew Chem Int Ed: https://doi.
org/10.1002/anie.202009717
43. Tao X, Kehr G, Wang X, Daniliuc CG, Grimme S, Erker G (2016) Rapid Dihydrogen Cleavage
by Persistent Nitroxide Radicals Under Frustrated Lewis Pair Conditions. Chem - Eur J
22:9504–9507. https://doi.org/10.1002/chem.201602058
44. Tao X, Daniliuc CG, Knitsch R, Hansen MR, Eckert H, Lübbesmeyer M, Studer A, Kehr G,
Erker G (2018) The Special Role of B(C 6 F 5 ) 3 in the Single Electron Reduction of Quinones
by Radicals. Chem Sci 9:8011–8018. https://doi.org/10.1039/C8SC03005G
45. Liu Y, Solari E, Scopelliti R, Fadaei Tirani F, Severin K (2018) Lewis Acid-Mediated OneElectron Reduction of Nitrous Oxide. Chem–Eur J 24:18809–18815. https://doi.org/10.1002/
chem.201804709
46. Bentley JN, Pradhan E, Zeng T, Caputo CB (2020) Bis(pentafluorophenyl)phenothiazylborane–
an Intramolecular Frustrated Lewis Pair Catalyst for Stannane Dehydrocoupling. Dalton Trans.
https://doi.org/10.1039/D0DT00506A
47. Waked AE, Ostadsharif Memar R, Stephan DW (2018) Nitrogen-Based Lewis Acids Derived
From Phosphonium Diazo Cations. Angew Chem Int Ed 57:11934–11938. https://doi.org/10.
1002/anie.201804183
48. Merk A, Großekappenberg H, Schmidtmann M, Luecke M, Lorent C, Driess M, Oestreich M,
Klare HFT, Müller T (2018) Single-Electron Transfer Reactions in Frustrated and Conventional
Silylium Ion/Phosphane Lewis Pairs. Angew Chem Int Ed 57:15267–15271. https://doi.org/
10.1002/anie.201808922
49. Dong Z, Pezzato C, Sienkiewicz A, Scopelliti R, Fadaei-Tirani F, Severin K (2020) SET
Processes in Lewis Acid–Base Reactions: The Tritylation of N-Heterocyclic Carbenes. Chem
Sci 11:7615-7618. https://doi.org/10.1039/D0SC01278E
50. Mulliken RS (1952) Molecular Compounds and Their Spectra. II. J Am Chem Soc 74:811–824.
https://doi.org/10.1021/ja01123a067
51. Foster R (1980) Electron Donor-Acceptor Complexes. J Phys Chem 84:2135–2141. https://
doi.org/10.1021/j100454a006
52. Rosokha SV, Kochi JK (2008) Fresh Look at Electron-Transfer Mechanisms via the
Donor/Acceptor Bindings in the Critical Encounter Complex. Acc Chem Res 41:641–653.
https://doi.org/10.1021/ar700256a
53. Hilinski EF, Masnovi JM, Amatore C, Kochi JK, Rentzepis PM (1983) Charge-Transfer Excitation of Electron Donor-Acceptor Complexes. Direct Observation of Ion Pairs by Time-Resolved
(Picosecond) Spectroscopy. J Am Chem Soc 105:6167–6168. https://doi.org/10.1021/ja0035
7a042
54. Hilinski EF, Masnovi JM, Kochi JK, Rentzepis PM (1984) Role of Ion Pairs in the Photochemistry of Electron Donor-Acceptor Complexes. Picosecond Spectroscopic Studies of AreneTetracyanoethylene Systems. J Am Chem Soc 106:8071–8077. https://doi.org/10.1021/ja0
0338a011
55. Connelly NG, Geiger WE (1996) Chemical Redox Agents for Organometallic Chemistry. Chem
Rev 96:877–910. https://doi.org/10.1021/cr940053x
56. Ramnial T, McKenzie I, Gorodetsky B, Tsang EMW, Clyburne JAC (2004) Reactions of NHeterocyclic Carbenes (NHCs) With One-Electron Oxidants: Possible Formation of a Carbene
Cation Radical. Chem Commun 1054. https://doi.org/10.1039/b314110a
385
41. Liu LL, Cao LL, Shao Y, Stephan DW (2017) Single Electron Delivery to Lewis Pairs: An
Avenue to Anions by Small Molecule Activation. J Am Chem Soc 139:10062–10071. https://
doi.org/10.1021/jacs.7b05120
42. Holtrop F, Jupp AR, Kooij B, van Leest NP, de Bruin B, Stephan DW, Slootweg JC (2020)
Single-Electron Transfer in Frustrated Lewis Pair Chemistry. Angew Chem Int Ed: https://doi.
org/10.1002/anie.202009717
43. Tao X, Kehr G, Wang X, Daniliuc CG, Grimme S, Erker G (2016) Rapid Dihydrogen Cleavage
by Persistent Nitroxide Radicals Under Frustrated Lewis Pair Conditions. Chem - Eur J
22:9504–9507. https://doi.org/10.1002/chem.201602058
44. Tao X, Daniliuc CG, Knitsch R, Hansen MR, Eckert H, Lübbesmeyer M, Studer A, Kehr G,
Erker G (2018) The Special Role of B(C 6 F 5 ) 3 in the Single Electron Reduction of Quinones
by Radicals. Chem Sci 9:8011–8018. https://doi.org/10.1039/C8SC03005G
45. Liu Y, Solari E, Scopelliti R, Fadaei Tirani F, Severin K (2018) Lewis Acid-Mediated OneElectron Reduction of Nitrous Oxide. Chem–Eur J 24:18809–18815. https://doi.org/10.1002/
chem.201804709
46. Bentley JN, Pradhan E, Zeng T, Caputo CB (2020) Bis(pentafluorophenyl)phenothiazylborane–
an Intramolecular Frustrated Lewis Pair Catalyst for Stannane Dehydrocoupling. Dalton Trans.
https://doi.org/10.1039/D0DT00506A
47. Waked AE, Ostadsharif Memar R, Stephan DW (2018) Nitrogen-Based Lewis Acids Derived
From Phosphonium Diazo Cations. Angew Chem Int Ed 57:11934–11938. https://doi.org/10.
1002/anie.201804183
48. Merk A, Großekappenberg H, Schmidtmann M, Luecke M, Lorent C, Driess M, Oestreich M,
Klare HFT, Müller T (2018) Single-Electron Transfer Reactions in Frustrated and Conventional
Silylium Ion/Phosphane Lewis Pairs. Angew Chem Int Ed 57:15267–15271. https://doi.org/
10.1002/anie.201808922
49. Dong Z, Pezzato C, Sienkiewicz A, Scopelliti R, Fadaei-Tirani F, Severin K (2020) SET
Processes in Lewis Acid–Base Reactions: The Tritylation of N-Heterocyclic Carbenes. Chem
Sci 11:7615-7618. https://doi.org/10.1039/D0SC01278E
50. Mulliken RS (1952) Molecular Compounds and Their Spectra. II. J Am Chem Soc 74:811–824.
https://doi.org/10.1021/ja01123a067
51. Foster R (1980) Electron Donor-Acceptor Complexes. J Phys Chem 84:2135–2141. https://
doi.org/10.1021/j100454a006
52. Rosokha SV, Kochi JK (2008) Fresh Look at Electron-Transfer Mechanisms via the
Donor/Acceptor Bindings in the Critical Encounter Complex. Acc Chem Res 41:641–653.
https://doi.org/10.1021/ar700256a
53. Hilinski EF, Masnovi JM, Amatore C, Kochi JK, Rentzepis PM (1983) Charge-Transfer Excitation of Electron Donor-Acceptor Complexes. Direct Observation of Ion Pairs by Time-Resolved
(Picosecond) Spectroscopy. J Am Chem Soc 105:6167–6168. https://doi.org/10.1021/ja0035
7a042
54. Hilinski EF, Masnovi JM, Kochi JK, Rentzepis PM (1984) Role of Ion Pairs in the Photochemistry of Electron Donor-Acceptor Complexes. Picosecond Spectroscopic Studies of AreneTetracyanoethylene Systems. J Am Chem Soc 106:8071–8077. https://doi.org/10.1021/ja0
0338a011
55. Connelly NG, Geiger WE (1996) Chemical Redox Agents for Organometallic Chemistry. Chem
Rev 96:877–910. https://doi.org/10.1021/cr940053x
56. Ramnial T, McKenzie I, Gorodetsky B, Tsang EMW, Clyburne JAC (2004) Reactions of NHeterocyclic Carbenes (NHCs) With One-Electron Oxidants: Possible Formation of a Carbene
Cation Radical. Chem Commun 1054. https://doi.org/10.1039/b314110a