10 Radicals in Frustrated Lewis Pair Chemistry
383
3. Stephan DW (2016) The Broadening Reach of Frustrated Lewis Pair Chemistry. Science
354:aaf7229. https://doi.org/10.1126/science.aaf7229
4. Stephan DW (2015) Frustrated Lewis Pairs. J Am Chem Soc 137:10018–10032. https://doi.
org/10.1021/jacs.5b06794
5. Jupp AR, Stephan DW (2019) New Directions for Frustrated Lewis Pair Chemistry. Trends
Chem 1:35–48. https://doi.org/10.1016/j.trechm.2019.01.006
6. Skara G, De Vleeschouwer F, Geerlings P, De Proft F, Pinter B (2017) Heterolytic Splitting of
Molecular Hydrogen by Frustrated and Classical Lewis Pairs: a Unified Reactivity Concept.
Sci Rep 7:16024. https://doi.org/10.1038/s41598-017-16244-1
7. Stephan DW, Erker G (2015) Frustrated Lewis Pair Chemistry: Development and Perspectives.
Angew Chem Int Ed 54:6400–6441. https://doi.org/10.1002/anie.201409800
8. Welch GC, Stephan DW (2007) Facile Heterolytic Cleavage of Dihydrogen by Phosphines and
Boranes. J Am Chem Soc 129:1880–1881. https://doi.org/10.1021/ja067961j
9. Chase PA, Jurca T, Stephan DW (2008) Lewis Acid-Catalyzed Hydrogenation: B(C 6 F 5 ) 3 -
Mediated Reduction of Imines and Nitriles with H 2 . Chem Commun 1701–1703. https://doi.
org/10.1039/B718598G
10. Spies P, Schwendemann S, Lange S, Kehr G, Fröhlich R, Erker G (2008) Metal-Free Catalytic
Hydrogenation of Enamines, Imines, and Conjugated Phosphinoalkenylboranes. Angew Chem
Int Ed 47:7543–7546. https://doi.org/10.1002/anie.200801432
11. Mahdi T, Stephan DW (2014) Enabling Catalytic Ketone Hydrogenation by Frustrated Lewis
Pairs. J Am Chem Soc 136:15809–15812. https://doi.org/10.1021/ja508829x
12. Greb L, Daniliuc C-G, Bergander K, Paradies J (2013) Functional-Group Tolerance in
Frustrated Lewis Pairs: Hydrogenation of Nitroolefins and Acrylates. Angew Chem Int Ed
52:5876–5879. https://doi.org/10.1002/anie.201210175
13. Paradies J (2014) Metal-Free Hydrogenation of Unsaturated Hydrocarbons Employing
Molecular Hydrogen. Angew Chem Int Ed 53:3552–3557. https://doi.org/10.1002/anie.201
309253
14. Scott DJ, Fuchter MJ, Ashley AE (2014) Nonmetal Catalyzed Hydrogenation of Carbonyl
Compounds. J Am Chem Soc 136:15813–15816. https://doi.org/10.1021/ja5088979
15. Paradies J (2019) Mechanisms in Frustrated Lewis Pair-Catalyzed Reactions. Eur J Org Chem
2019:283–294. https://doi.org/10.1002/ejoc.201800944
16. Liu LL, Cao LL, Zhu D, Zhou J, Stephan DW (2018) Homolytic Cleavage of Peroxide Bonds
via a Single Electron Transfer of a Frustrated Lewis Pair. Chem Commun 54:7431–7434.
https://doi.org/10.1039/C8CC03522A
17. Liu L, (Leo), Cao LL, Shao Y, Ménard G, Stephan DW, (2017) A Radical Mechanism for
Frustrated Lewis Pair Reactivity. Chem 3:259–267. https://doi.org/10.1016/j.chempr.2017.
05.022
18. Rocchigiani L, Ciancaleoni G, Zuccaccia C, Macchioni A (2014) Probing the Association of
Frustrated Phosphine-Borane Lewis Pairs in Solution by NMR Spectroscopy. J Am Chem Soc
136:112–115. https://doi.org/10.1021/ja4119169
19. Rokob TA, Bakó I, Stirling A, Hamza A, Pápai I (2013) Reactivity Models of Hydrogen
Activation by Frustrated Lewis Pairs: Synergistic Electron Transfers or Polarization by Electric
Field? J Am Chem Soc 135:4425–4437. https://doi.org/10.1021/ja312387q
20. Grimme S, Kruse H, Goerigk L, Erker G (2010) The Mechanism of Dihydrogen Activation
by Frustrated Lewis Pairs Revisited. Angew Chem Int Ed 49:1402–1405. https://doi.org/10.
1002/anie.200905484
21. Daru J, Bakó I, Stirling A, Pápai I (2019) Mechanism of Heterolytic Hydrogen Splitting by
Frustrated Lewis Pairs: Comparison of Static and Dynamic Models. ACS Catal 9:6049–6057.
https://doi.org/10.1021/acscatal.9b01137
22. Lawrence EJ, Oganesyan VS, Wildgoose GG, Ashley AE (2012) Exploring the Fate of the
Tris(pentafluorophenyl)borane Radical Anion in Weakly Coordinating Solvents. Dalton Trans
42:782–789. https://doi.org/10.1039/C2DT31622F
23. Piers WE, Marwitz AJV, Mercier LG (2011) Mechanistic Aspects of Bond Activation with
Perfluoroarylboranes. Inorg Chem 50:12252–12262. https://doi.org/10.1021/ic2006474
383
3. Stephan DW (2016) The Broadening Reach of Frustrated Lewis Pair Chemistry. Science
354:aaf7229. https://doi.org/10.1126/science.aaf7229
4. Stephan DW (2015) Frustrated Lewis Pairs. J Am Chem Soc 137:10018–10032. https://doi.
org/10.1021/jacs.5b06794
5. Jupp AR, Stephan DW (2019) New Directions for Frustrated Lewis Pair Chemistry. Trends
Chem 1:35–48. https://doi.org/10.1016/j.trechm.2019.01.006
6. Skara G, De Vleeschouwer F, Geerlings P, De Proft F, Pinter B (2017) Heterolytic Splitting of
Molecular Hydrogen by Frustrated and Classical Lewis Pairs: a Unified Reactivity Concept.
Sci Rep 7:16024. https://doi.org/10.1038/s41598-017-16244-1
7. Stephan DW, Erker G (2015) Frustrated Lewis Pair Chemistry: Development and Perspectives.
Angew Chem Int Ed 54:6400–6441. https://doi.org/10.1002/anie.201409800
8. Welch GC, Stephan DW (2007) Facile Heterolytic Cleavage of Dihydrogen by Phosphines and
Boranes. J Am Chem Soc 129:1880–1881. https://doi.org/10.1021/ja067961j
9. Chase PA, Jurca T, Stephan DW (2008) Lewis Acid-Catalyzed Hydrogenation: B(C 6 F 5 ) 3 -
Mediated Reduction of Imines and Nitriles with H 2 . Chem Commun 1701–1703. https://doi.
org/10.1039/B718598G
10. Spies P, Schwendemann S, Lange S, Kehr G, Fröhlich R, Erker G (2008) Metal-Free Catalytic
Hydrogenation of Enamines, Imines, and Conjugated Phosphinoalkenylboranes. Angew Chem
Int Ed 47:7543–7546. https://doi.org/10.1002/anie.200801432
11. Mahdi T, Stephan DW (2014) Enabling Catalytic Ketone Hydrogenation by Frustrated Lewis
Pairs. J Am Chem Soc 136:15809–15812. https://doi.org/10.1021/ja508829x
12. Greb L, Daniliuc C-G, Bergander K, Paradies J (2013) Functional-Group Tolerance in
Frustrated Lewis Pairs: Hydrogenation of Nitroolefins and Acrylates. Angew Chem Int Ed
52:5876–5879. https://doi.org/10.1002/anie.201210175
13. Paradies J (2014) Metal-Free Hydrogenation of Unsaturated Hydrocarbons Employing
Molecular Hydrogen. Angew Chem Int Ed 53:3552–3557. https://doi.org/10.1002/anie.201
309253
14. Scott DJ, Fuchter MJ, Ashley AE (2014) Nonmetal Catalyzed Hydrogenation of Carbonyl
Compounds. J Am Chem Soc 136:15813–15816. https://doi.org/10.1021/ja5088979
15. Paradies J (2019) Mechanisms in Frustrated Lewis Pair-Catalyzed Reactions. Eur J Org Chem
2019:283–294. https://doi.org/10.1002/ejoc.201800944
16. Liu LL, Cao LL, Zhu D, Zhou J, Stephan DW (2018) Homolytic Cleavage of Peroxide Bonds
via a Single Electron Transfer of a Frustrated Lewis Pair. Chem Commun 54:7431–7434.
https://doi.org/10.1039/C8CC03522A
17. Liu L, (Leo), Cao LL, Shao Y, Ménard G, Stephan DW, (2017) A Radical Mechanism for
Frustrated Lewis Pair Reactivity. Chem 3:259–267. https://doi.org/10.1016/j.chempr.2017.
05.022
18. Rocchigiani L, Ciancaleoni G, Zuccaccia C, Macchioni A (2014) Probing the Association of
Frustrated Phosphine-Borane Lewis Pairs in Solution by NMR Spectroscopy. J Am Chem Soc
136:112–115. https://doi.org/10.1021/ja4119169
19. Rokob TA, Bakó I, Stirling A, Hamza A, Pápai I (2013) Reactivity Models of Hydrogen
Activation by Frustrated Lewis Pairs: Synergistic Electron Transfers or Polarization by Electric
Field? J Am Chem Soc 135:4425–4437. https://doi.org/10.1021/ja312387q
20. Grimme S, Kruse H, Goerigk L, Erker G (2010) The Mechanism of Dihydrogen Activation
by Frustrated Lewis Pairs Revisited. Angew Chem Int Ed 49:1402–1405. https://doi.org/10.
1002/anie.200905484
21. Daru J, Bakó I, Stirling A, Pápai I (2019) Mechanism of Heterolytic Hydrogen Splitting by
Frustrated Lewis Pairs: Comparison of Static and Dynamic Models. ACS Catal 9:6049–6057.
https://doi.org/10.1021/acscatal.9b01137
22. Lawrence EJ, Oganesyan VS, Wildgoose GG, Ashley AE (2012) Exploring the Fate of the
Tris(pentafluorophenyl)borane Radical Anion in Weakly Coordinating Solvents. Dalton Trans
42:782–789. https://doi.org/10.1039/C2DT31622F
23. Piers WE, Marwitz AJV, Mercier LG (2011) Mechanistic Aspects of Bond Activation with
Perfluoroarylboranes. Inorg Chem 50:12252–12262. https://doi.org/10.1021/ic2006474