230
T. A. Gazis et al.
archetypical B(C 6 F 5 ) 3 . Despite the fact that the chemistry of these boranes is still in
its infancy, these new boranes have already found widespread application in synthetic
transformations including enantioselective reactions.
References
1. Welch GC, San Juan RR, Masuda JD, Stephan DW (2006) Reversible, Metal-Free Hydrogen
Activation. Science 314:1124–1126. https://doi.org/10.1126/science.1134230
2. Spies P, Erker G, Kehr G, Bergander K, Fröhlich R, Grimme S, Stephan DW (2007)
Rapid Intramolecular Heterolytic Dihydrogen Activation by a Four-Membered Heterocyclic
Phosphane–Borane Adduct. Chem Commun 5072–5074. https://doi.org/10.1039/b710475h
3. 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
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. 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
6. 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
7. Stephan DW (2016) The Broadening Reach of Frustrated Lewis Pair Chemistry. Science
354:aaf7229. https://doi.org/10.1126/science.aaf7229
8. 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
9. Stephan DW (2008) “Frustrated Lewis Pairs”: a Concept for New Reactivity and Catalysis.
Org Biomol Chem 6:1535–1539. https://doi.org/10.1039/b802575b
10. Paradies J (2013) Frustrated Lewis Pair Catalyzed Hydrogenations. Synlett 24:777–780.
https://doi.org/10.1055/s-0032-1318312
11. Stephan DW, Erker G (2013) Frustrated Lewis Pairs I: Uncovering and Understanding. Top
Curr Chem 332:85–110. https://doi.org/10.1007/128_2012_392
12. Erker G, Stephan DW (2013) Frustrated Lewis Pairs II: Expanding the Scope. Top Curr Chem
334:1–345. https://doi.org/10.1007/978-3-642-37759-4
13. Stephan DW (2015) Frustrated Lewis Pairs. J Am Chem Soc 137:10018–10032. https://doi.
org/10.1021/jacs.5b06794
14. 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
15. Paradies J (2019) Mechanisms in Frustrated Lewis Pair-Catalyzed Reactions. Eur J Org Chem
283–294. https://doi.org/10.1002/ejoc.201800944
16. Greb L (2018) Lewis Superacids: Classifications, Candidates, and Applications. Chem Eur J
24:17881–17896. https://doi.org/10.1002/chem.201802698
17. Gaffen JR, Bentley JN, Torres LC, Chu C, Baumgartner T, Caputo CB (2019) A Simple and
Effective Method of Determining Lewis Acidity by Using Fluorescence. Chem 5:1567–1583.
https://doi.org/10.1016/j.chempr.2019.03.022
18. Willcox D, Melen RL (2019) Illuminating Lewis Acidity Strength. Chem 5:1362–1363.
https://doi.org/10.1016/j.chempr.2019.04.001
19. Mayer U, Gutmann V, Gerger W (1975) The Acceptor Number — A Quantitative Empirical
Parameter for the Electrophilic Properties of Solvents. Monatsh Chem 106:1235–1257
20. Beckett MA, Strickland GC, Holland JR, Sukumar Varma K (1996) A Convenient NMR
Method for the Measurement of Lewis Acidity at Boron Centres: Correlation of Reaction Rates
of Lewis Acid Initiated Epoxide Polymerizations with Lewis Acidity. Polymer 37:4629–4631.
https://doi.org/10.1016/0032-3861(96)00323-0
T. A. Gazis et al.
archetypical B(C 6 F 5 ) 3 . Despite the fact that the chemistry of these boranes is still in
its infancy, these new boranes have already found widespread application in synthetic
transformations including enantioselective reactions.
References
1. Welch GC, San Juan RR, Masuda JD, Stephan DW (2006) Reversible, Metal-Free Hydrogen
Activation. Science 314:1124–1126. https://doi.org/10.1126/science.1134230
2. Spies P, Erker G, Kehr G, Bergander K, Fröhlich R, Grimme S, Stephan DW (2007)
Rapid Intramolecular Heterolytic Dihydrogen Activation by a Four-Membered Heterocyclic
Phosphane–Borane Adduct. Chem Commun 5072–5074. https://doi.org/10.1039/b710475h
3. 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
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. 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
6. 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
7. Stephan DW (2016) The Broadening Reach of Frustrated Lewis Pair Chemistry. Science
354:aaf7229. https://doi.org/10.1126/science.aaf7229
8. 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
9. Stephan DW (2008) “Frustrated Lewis Pairs”: a Concept for New Reactivity and Catalysis.
Org Biomol Chem 6:1535–1539. https://doi.org/10.1039/b802575b
10. Paradies J (2013) Frustrated Lewis Pair Catalyzed Hydrogenations. Synlett 24:777–780.
https://doi.org/10.1055/s-0032-1318312
11. Stephan DW, Erker G (2013) Frustrated Lewis Pairs I: Uncovering and Understanding. Top
Curr Chem 332:85–110. https://doi.org/10.1007/128_2012_392
12. Erker G, Stephan DW (2013) Frustrated Lewis Pairs II: Expanding the Scope. Top Curr Chem
334:1–345. https://doi.org/10.1007/978-3-642-37759-4
13. Stephan DW (2015) Frustrated Lewis Pairs. J Am Chem Soc 137:10018–10032. https://doi.
org/10.1021/jacs.5b06794
14. 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
15. Paradies J (2019) Mechanisms in Frustrated Lewis Pair-Catalyzed Reactions. Eur J Org Chem
283–294. https://doi.org/10.1002/ejoc.201800944
16. Greb L (2018) Lewis Superacids: Classifications, Candidates, and Applications. Chem Eur J
24:17881–17896. https://doi.org/10.1002/chem.201802698
17. Gaffen JR, Bentley JN, Torres LC, Chu C, Baumgartner T, Caputo CB (2019) A Simple and
Effective Method of Determining Lewis Acidity by Using Fluorescence. Chem 5:1567–1583.
https://doi.org/10.1016/j.chempr.2019.03.022
18. Willcox D, Melen RL (2019) Illuminating Lewis Acidity Strength. Chem 5:1362–1363.
https://doi.org/10.1016/j.chempr.2019.04.001
19. Mayer U, Gutmann V, Gerger W (1975) The Acceptor Number — A Quantitative Empirical
Parameter for the Electrophilic Properties of Solvents. Monatsh Chem 106:1235–1257
20. Beckett MA, Strickland GC, Holland JR, Sukumar Varma K (1996) A Convenient NMR
Method for the Measurement of Lewis Acidity at Boron Centres: Correlation of Reaction Rates
of Lewis Acid Initiated Epoxide Polymerizations with Lewis Acidity. Polymer 37:4629–4631.
https://doi.org/10.1016/0032-3861(96)00323-0