2 Frustrated Lewis Pair Catalyzed Asymmetric Reactions
83
still remain some problems and challenges for this emerging area, such as the difficulty for the catalyst synthesis, the relatively narrow substrate scope, the efficiency,
and the selectivity. To develop novel catalysts as well as novel strategies for the
catalyst synthesis and expanding their application for asymmetric reduction of other
unsaturated compounds are undoubtedly very important tasks to ensure the wide
acceptance and application of FLPs in synthetic chemistry.
References
1. Welch GC et al (2006) Reversible, Metal-Free Hydrogen Activation. Science 314(5802):1124–
1126. https://doi.org/10.1126/science.1134230
2. Kenward AL, Piers WE (2008) Heterolytic H 2 Activation by Nonmetals. Angew Chem Int Ed
47:38–41. https://doi.org/10.1002/anie.200702816
3. Stephan DW (2009) Frustrated Lewis Pairs: a New Strategy to Small Molecule Activation and
Hydrogenation Catalysis. Dalton Trans 3129–3136. https://doi.org/10.1039/B819621D
4. Stephan DW, Erker G (2010) Frustrated Lewis Pairs: Metal-Free Hydrogen Activation and
More. Angew Chem Int Ed 49:46–76. https://doi.org/10.1002/anie.200903708
5. Erker G (2011) Organometallic Frustrated Lewis Pair Chemistry. Dalton Trans 40:7475–
7483. https://doi.org/10.1039/C1DT10152H
6. Soós T (2011) Design of Frustrated Lewis Pair Catalysts for Metal-Free and Selective
Hydrogenation. Pure Appl Chem 83:667–675. https://doi.org/10.1351/PAC-CON-11-01-02
7. Erker G (2012) Frustrated Lewis Pairs: Some Recent Developments. Pure Appl Chem 84:2203–
2217. https://doi.org/10.1351/PAC-CON-12-04-07
8. 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
9. 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
10. Oestreich M, Hermeke J, Mohr J (2015) A Unified Survey of Si–H and H–H Bond Activation
Catalysed by Electron-Deficient Boranes. Chem Soc Rev 44:2202–2220. https://doi.org/10.
1039/C4CS00451E
11. Stephan DW (2015) Frustrated Lewis Pairs: From Concept to Catalysis. Acc Chem Res 48:306–
316. https://doi.org/10.1021/ar500375j
12. Scott DJ, Fuchter MJ, Ashley AE (2017) Designing Effective “Frustrated Lewis Pair”
Hydrogenation Catalysts. Chem Soc Rev 46:5689–5700. https://doi.org/10.1039/C7CS00154A
13. Liu Y, Du H (2014) Frustrated Lewis Pair Catalyzed Asymmetric Hydrogenation. Acta Chim
Sinica 72:771–777. https://doi.org/10.6023/A14040344
14. Feng X, Du H (2014) Metal-Free Asymmetric Hydrogenation and Hydrosilylation Catalyzed by
Frustrated Lewis Pairs. Tetrahedron Lett 55:6959–6964. https://doi.org/10.1016/j.tetlet.2014.
10.138
15. Shi L, Zhou Y-G (2015) Enantioselective Metal-Free Hydrogenation Catalyzed by Chiral
Frustrated Lewis Pairs. ChemCatChem 7:54–56. https://doi.org/10.1002/cctc.201402838
16. Wilkins LC, Melen RL (2016) Enantioselective Main Group Catalysis: Modern Catalysts for
Organic Transformations. Coord Chem Rev 324:123–139. https://doi.org/10.1016/j.ccr.2016.
07.011
17. Paradies J (2018) Chiral Borane-Based Lewis Acids for Metal Free Hydrogenations. Top
Organomet Chem 62:193–216. https://doi.org/10.1007/3418_2016_173
18. Meng W, Feng X, Du H (2018) Frustrated Lewis Pairs Catalyzed Asymmetric Metal-Free
Hydrogenations and Hydrosilylations. Acc Chem Res 51:191–201. https://doi.org/10.1021/
acs.accounts.7b00530
83
still remain some problems and challenges for this emerging area, such as the difficulty for the catalyst synthesis, the relatively narrow substrate scope, the efficiency,
and the selectivity. To develop novel catalysts as well as novel strategies for the
catalyst synthesis and expanding their application for asymmetric reduction of other
unsaturated compounds are undoubtedly very important tasks to ensure the wide
acceptance and application of FLPs in synthetic chemistry.
References
1. Welch GC et al (2006) Reversible, Metal-Free Hydrogen Activation. Science 314(5802):1124–
1126. https://doi.org/10.1126/science.1134230
2. Kenward AL, Piers WE (2008) Heterolytic H 2 Activation by Nonmetals. Angew Chem Int Ed
47:38–41. https://doi.org/10.1002/anie.200702816
3. Stephan DW (2009) Frustrated Lewis Pairs: a New Strategy to Small Molecule Activation and
Hydrogenation Catalysis. Dalton Trans 3129–3136. https://doi.org/10.1039/B819621D
4. Stephan DW, Erker G (2010) Frustrated Lewis Pairs: Metal-Free Hydrogen Activation and
More. Angew Chem Int Ed 49:46–76. https://doi.org/10.1002/anie.200903708
5. Erker G (2011) Organometallic Frustrated Lewis Pair Chemistry. Dalton Trans 40:7475–
7483. https://doi.org/10.1039/C1DT10152H
6. Soós T (2011) Design of Frustrated Lewis Pair Catalysts for Metal-Free and Selective
Hydrogenation. Pure Appl Chem 83:667–675. https://doi.org/10.1351/PAC-CON-11-01-02
7. Erker G (2012) Frustrated Lewis Pairs: Some Recent Developments. Pure Appl Chem 84:2203–
2217. https://doi.org/10.1351/PAC-CON-12-04-07
8. 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
9. 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
10. Oestreich M, Hermeke J, Mohr J (2015) A Unified Survey of Si–H and H–H Bond Activation
Catalysed by Electron-Deficient Boranes. Chem Soc Rev 44:2202–2220. https://doi.org/10.
1039/C4CS00451E
11. Stephan DW (2015) Frustrated Lewis Pairs: From Concept to Catalysis. Acc Chem Res 48:306–
316. https://doi.org/10.1021/ar500375j
12. Scott DJ, Fuchter MJ, Ashley AE (2017) Designing Effective “Frustrated Lewis Pair”
Hydrogenation Catalysts. Chem Soc Rev 46:5689–5700. https://doi.org/10.1039/C7CS00154A
13. Liu Y, Du H (2014) Frustrated Lewis Pair Catalyzed Asymmetric Hydrogenation. Acta Chim
Sinica 72:771–777. https://doi.org/10.6023/A14040344
14. Feng X, Du H (2014) Metal-Free Asymmetric Hydrogenation and Hydrosilylation Catalyzed by
Frustrated Lewis Pairs. Tetrahedron Lett 55:6959–6964. https://doi.org/10.1016/j.tetlet.2014.
10.138
15. Shi L, Zhou Y-G (2015) Enantioselective Metal-Free Hydrogenation Catalyzed by Chiral
Frustrated Lewis Pairs. ChemCatChem 7:54–56. https://doi.org/10.1002/cctc.201402838
16. Wilkins LC, Melen RL (2016) Enantioselective Main Group Catalysis: Modern Catalysts for
Organic Transformations. Coord Chem Rev 324:123–139. https://doi.org/10.1016/j.ccr.2016.
07.011
17. Paradies J (2018) Chiral Borane-Based Lewis Acids for Metal Free Hydrogenations. Top
Organomet Chem 62:193–216. https://doi.org/10.1007/3418_2016_173
18. Meng W, Feng X, Du H (2018) Frustrated Lewis Pairs Catalyzed Asymmetric Metal-Free
Hydrogenations and Hydrosilylations. Acc Chem Res 51:191–201. https://doi.org/10.1021/
acs.accounts.7b00530