1 Frustrated Lewis Pair Catalysis: An Introduction
21
15. Weicker SA, Stephan DW (2015) Main Group Lewis Acids in Frustrated Lewis Pair Chemistry: Beyond Electrophilic Boranes. Bull Chem Soc Jpn 88(8):1003–1016. https://doi.org/
10.1246/bcsj.20150131
16. Paradies J (2013) Frustrated Lewis Pair Catalyzed Hydrogenations. Synlett 24(7):777–780.
https://doi.org/10.1055/s-0032-1318312
17. Hounjet LJ, Stephan DW (2014) Hydrogenation by Frustrated Lewis Pairs: Main Group
Alternatives to Transition Metal Catalysts? Org Process Res Dev 18(3):385–391. https://doi.
org/10.1021/Op400315m
18. Chase PA, Welch GC, Jurca T, Stephan DW (2007) Metal-Free Catalytic Hydrogenation.
Angew Chem Int Ed 46(42):8050–8053. https://doi.org/10.1002/anie.200702908
19. 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 14:1701–1703. https://
doi.org/10.1039/B718598g
20. Mahdi T, Stephan DW (2014) Enabling Catalytic Ketone Hydrogenation by Frustrated Lewis
Pairs. J Am Chem Soc 136(45):15809–15812. https://doi.org/10.1021/ja508829x
21. Scott DJ, Fuchter MJ, Ashley AE (2014) Nonmetal Catalyzed Hydrogenation of Carbonyl
Compounds. J Am Chem Soc 136(45):15813–15816. https://doi.org/10.1021/ja5088979
22. Inés B, Palomas D, Holle S, Steinberg S, Nicasio JA, Alcarazo M (2012) Metal-Free Hydrogenation of Electron-Poor Allenes and Alkenes. Angew Chem Int Ed 51(49):12367–12369.
https://doi.org/10.1002/anie.201205348
23. Greb L, Daniliuc CG, Bergander K, Paradies J (2013) Functional-Group Tolerance in Frustrated Lewis Pairs: Hydrogenation of Nitroolefins and Acrylates. Angew Chem Int Ed
52(22):5876–5879. https://doi.org/10.1002/anie.201210175
24. 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(39):7543–7546. https://doi.org/10.1002/anie.200801432
25. Axenov KV, Kehr G, Fröhlich R, Erker G (2009) Catalytic Hydrogenation of Sensitive
Organometallic Compounds by Antagonistic N/B Lewis Pair Catalyst Systems. J Am Chem
Soc 131(10):3454–3455. https://doi.org/10.1021/Ja8100006
26. Wang HD, Fröhlich R, Kehr G, Erker G (2008) Heterolytic Dihydrogen Activation with the
1,8-Bis(diphenylphosphino)-naphthalene/B(C 6 F 5 ) 3 Pair and its Application for Metal-Free
Catalytic Hydrogenation of Silyl Enol Ethers. Chem Commun 45:5966–5968. https://doi.
org/10.1039/B813286k
27. Jiang C, Blacque O, Berke H (2009) Metal-Free Hydrogen Activation and Hydrogenation of Imines by 1,8-Bis(dipentafluorophenylboryl)naphthalene. Chem Commun 5518–
5520. https://doi.org/10.1039/B909620E
28. Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown
CC, Heiden ZM, Welch GC, Ullrich M (2011) Metal-Free Catalytic Hydrogenation of Polar
Substrates by Frustrated Lewis Pairs. Inorg Chem 50:12338–12348. https://doi.org/10.1021/
ic200663v
29. Zhu X, Du H (2015) A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the
Synthesis of cis-Vicinal Diamines. Org Lett 17:3106–3109. https://doi.org/10.1021/acs.org
lett.5b01380
30. Mohr J, Oestreich M (2014) B(C 6 F 5 ) 3 -Catalyzed Hydrogenation of Oxime Ethers Without
Cleavage of the N-O Bond. Angew Chem Int Ed 53(48):13278–13281. https://doi.org/10.
1002/anie.201407324
31. Mohr J, Porwal D, Chatterjee I, Oestreich M (2015) Extending the Scope of the B(C 6 F 5 ) 3 -
Catalyzed CN Bond Reduction: Hydrogenation of Oxime Ethers and Hydrazones. Chem Eur
J 21:17583–17586. https://doi.org/10.1002/chem.201503509
32. Xu BH, Kehr G, Frohlich R, Wibbeling B, Schirmer B, Grimme S, Erker G (2011) Reaction
of Frustrated Lewis Pairs with Conjugated Ynones-Selective Hydrogenation of the CarbonCarbon Triple Bond. Angew Chem Int Ed 50(31):7183–7186. https://doi.org/10.1002/anie.
201101051
21
15. Weicker SA, Stephan DW (2015) Main Group Lewis Acids in Frustrated Lewis Pair Chemistry: Beyond Electrophilic Boranes. Bull Chem Soc Jpn 88(8):1003–1016. https://doi.org/
10.1246/bcsj.20150131
16. Paradies J (2013) Frustrated Lewis Pair Catalyzed Hydrogenations. Synlett 24(7):777–780.
https://doi.org/10.1055/s-0032-1318312
17. Hounjet LJ, Stephan DW (2014) Hydrogenation by Frustrated Lewis Pairs: Main Group
Alternatives to Transition Metal Catalysts? Org Process Res Dev 18(3):385–391. https://doi.
org/10.1021/Op400315m
18. Chase PA, Welch GC, Jurca T, Stephan DW (2007) Metal-Free Catalytic Hydrogenation.
Angew Chem Int Ed 46(42):8050–8053. https://doi.org/10.1002/anie.200702908
19. 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 14:1701–1703. https://
doi.org/10.1039/B718598g
20. Mahdi T, Stephan DW (2014) Enabling Catalytic Ketone Hydrogenation by Frustrated Lewis
Pairs. J Am Chem Soc 136(45):15809–15812. https://doi.org/10.1021/ja508829x
21. Scott DJ, Fuchter MJ, Ashley AE (2014) Nonmetal Catalyzed Hydrogenation of Carbonyl
Compounds. J Am Chem Soc 136(45):15813–15816. https://doi.org/10.1021/ja5088979
22. Inés B, Palomas D, Holle S, Steinberg S, Nicasio JA, Alcarazo M (2012) Metal-Free Hydrogenation of Electron-Poor Allenes and Alkenes. Angew Chem Int Ed 51(49):12367–12369.
https://doi.org/10.1002/anie.201205348
23. Greb L, Daniliuc CG, Bergander K, Paradies J (2013) Functional-Group Tolerance in Frustrated Lewis Pairs: Hydrogenation of Nitroolefins and Acrylates. Angew Chem Int Ed
52(22):5876–5879. https://doi.org/10.1002/anie.201210175
24. 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(39):7543–7546. https://doi.org/10.1002/anie.200801432
25. Axenov KV, Kehr G, Fröhlich R, Erker G (2009) Catalytic Hydrogenation of Sensitive
Organometallic Compounds by Antagonistic N/B Lewis Pair Catalyst Systems. J Am Chem
Soc 131(10):3454–3455. https://doi.org/10.1021/Ja8100006
26. Wang HD, Fröhlich R, Kehr G, Erker G (2008) Heterolytic Dihydrogen Activation with the
1,8-Bis(diphenylphosphino)-naphthalene/B(C 6 F 5 ) 3 Pair and its Application for Metal-Free
Catalytic Hydrogenation of Silyl Enol Ethers. Chem Commun 45:5966–5968. https://doi.
org/10.1039/B813286k
27. Jiang C, Blacque O, Berke H (2009) Metal-Free Hydrogen Activation and Hydrogenation of Imines by 1,8-Bis(dipentafluorophenylboryl)naphthalene. Chem Commun 5518–
5520. https://doi.org/10.1039/B909620E
28. Stephan DW, Greenberg S, Graham TW, Chase P, Hastie JJ, Geier SJ, Farrell JM, Brown
CC, Heiden ZM, Welch GC, Ullrich M (2011) Metal-Free Catalytic Hydrogenation of Polar
Substrates by Frustrated Lewis Pairs. Inorg Chem 50:12338–12348. https://doi.org/10.1021/
ic200663v
29. Zhu X, Du H (2015) A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the
Synthesis of cis-Vicinal Diamines. Org Lett 17:3106–3109. https://doi.org/10.1021/acs.org
lett.5b01380
30. Mohr J, Oestreich M (2014) B(C 6 F 5 ) 3 -Catalyzed Hydrogenation of Oxime Ethers Without
Cleavage of the N-O Bond. Angew Chem Int Ed 53(48):13278–13281. https://doi.org/10.
1002/anie.201407324
31. Mohr J, Porwal D, Chatterjee I, Oestreich M (2015) Extending the Scope of the B(C 6 F 5 ) 3 -
Catalyzed CN Bond Reduction: Hydrogenation of Oxime Ethers and Hydrazones. Chem Eur
J 21:17583–17586. https://doi.org/10.1002/chem.201503509
32. Xu BH, Kehr G, Frohlich R, Wibbeling B, Schirmer B, Grimme S, Erker G (2011) Reaction
of Frustrated Lewis Pairs with Conjugated Ynones-Selective Hydrogenation of the CarbonCarbon Triple Bond. Angew Chem Int Ed 50(31):7183–7186. https://doi.org/10.1002/anie.
201101051