204
M. Heshmat et al.
14. Weicker SA, Stephan DW (2015) Main Group Lewis Acids in Frustrated Lewis Pair Chemistry: Beyond Electrophilic Boranes. Bull Chem Soc Jpn 88:1003–1016. https://doi.org/10.
1246/bcsj.20150131
15. Dureen MA, Stephan DW (2009) Terminal Alkyne Activation by Frustrated and Classical
Lewis Acid/Phosphine Pairs. J Am Chem Soc 131:8396–8397. https://doi.org/10.1021/ja9
03650w
16. Keweloh L, Klöcker H, Würthwein EU, Uhl W (2016) A P-H Functionalized Al/P Frustrated Lewis Pair: Substrate Activation and Selective Hydrogen Transfer. Angew Chem Int
Ed 55:3212–3215. https://doi.org/10.1002/anie.201511048
17. Zheng W, Pi C, Wu H (2012) An Alkynylaminomethylaluminum Species with a SixMembered Chair Conformation Al 2 C 2 N 2 Framework: A New Path to Geminal N/Al
Frustrated Lewis Pairs. Organometallics 31:4072–4075. https://doi.org/10.1021/om200967e
18. El-Hamdi M, Timoshkin AY (2019) Hydrogen Splitting by Pyramidalized 13–15 DonorAcceptor Cryptands: a Computational Study. J Comp Chem 40:1892–1901. https://doi.org/
10.1002/jcc.25845
19. Li Z, Guo J, Lu Y, Hu W, Dang Y, Wang ZX (2018) A Strategy for Developing MetalFree Hydrogenantion Catalysts: a DFT Proof-of-Principle Study. Dalton Trans 47:7709–
7714. https://doi.org/10.1039/C8DT01619D
20. Li W, Li C, Lyu Y (2019) A Computational Mechanistic Insight into H 2 Activation and
CO 2 Reduction over β-Diketiminato-ligand Group 13 Metal Complexes. J Catalysis 373:1–
12. https://doi.org/10.1016/j.jcat.2019.03.029
21. Lam J, Szkop KM, Mosaferi E, Stephan DW (2019) FLP Catalysis: Main Group Hydrogenations of Organic Unsaturated Substrates. Chem Soc Rev 48:3592–3612. https://doi.org/10.
1039/C8CS00277K
22. McCahill JSJ, Welch GC, Stephan DW (2007) Reactivity of ‘Frustrated Lewis Pairs’: ThreeComponent Reactions of Phosphines, a Borane, and Olefins. Angew Chem Int Ed 46:4968–
4971. https://doi.org/10.1002/anie.200701215
23. Knitsch R, Özgün T, Chen GQ, Kehr G, Erker G, Hansen MR, Eckert H (2019) Dihydrogen
Splitting by Intramolecular Borane-Phosphane Frustrated Lewis Pairs: A Comprehensive
Characterization Strategy Using Solid State NMR and DFT Calculations. ChemPhysChem
20:1837–1849. https://doi.org/10.1002/cphc.201900406
24. Whittell G, Balmond EI, Robertson AP, Patra SK, Haddow MF, Manners I (2010) Reaction
of Amine-Borane Adducts with Frustrated Lewis Pair Combinations of Group 14 Triflates
and Sterically Hindered Nitrogen Bases. Eur J Inorg Chem 2010:3967–3975. https://doi.org/
10.1002/ejic.201000515
25. Scott DJ, Phillip NA, Sapsford JS, Deacy AC, Fuchter MJ Ashley AE (2016) Versatile Catalytic Hydrogenation using a Simple Tin(IV) Lewis Acid. Angew Chem Int Ed
55:14738–14742. https://doi.org/10.1002/anie.201606639
26. Cooper RT, Sapsford JS, Turnell-Ritson RC, Hyon DH, White AJP, Ashley AE (2017)
Hydrogen Activation using a Novel Tribenzyltin Lewis Acid. Phil Trans R Soc A
375:20170008. https://doi.org/10.1098/rsta.2017.0008
27. Das S, Mondal S, Pati SK (2018) Mechanistic Insight into Hydrogen Activation by Frustrated
N/Sn Lewis Pairs. Chem Eur J 24:2575–2579. https://doi.org/10.1002/chem.201705861
28. Hounjet LJ, Bannwarth C, Garon CN, Caputo CB, Grimme S, Stephan DW (2013) Combinations of Ethers and B(C 6 F 5 ) 3 Function as Hydrogenation Catalysts. Angew Chem Int Ed
52:7492–7495. https://doi.org/10.1002/anie.201303166
29. 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
30. 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
31. Bannwarth C, Hansen A, Grimme S (2015) The Association of Two “Frustrated” Lewis Pairs
by State-of-the-Art Quantum Chemical Methods. Isr J Chem 55:235–242. https://doi.org/10.
1002/ijch.201400138
32. Bistoni G, Auer AA, Neese F (2017) Understanding the Role of Dispersion in Frustrated Lewis
Pairs and Classical Lewis Adducts: A Domain-Based Local Pair Natural Orbital Coupled
Cluster Study. Chem Eur J 23:865–873. https://doi.org/10.1002/chem.201604127
M. Heshmat et al.
14. Weicker SA, Stephan DW (2015) Main Group Lewis Acids in Frustrated Lewis Pair Chemistry: Beyond Electrophilic Boranes. Bull Chem Soc Jpn 88:1003–1016. https://doi.org/10.
1246/bcsj.20150131
15. Dureen MA, Stephan DW (2009) Terminal Alkyne Activation by Frustrated and Classical
Lewis Acid/Phosphine Pairs. J Am Chem Soc 131:8396–8397. https://doi.org/10.1021/ja9
03650w
16. Keweloh L, Klöcker H, Würthwein EU, Uhl W (2016) A P-H Functionalized Al/P Frustrated Lewis Pair: Substrate Activation and Selective Hydrogen Transfer. Angew Chem Int
Ed 55:3212–3215. https://doi.org/10.1002/anie.201511048
17. Zheng W, Pi C, Wu H (2012) An Alkynylaminomethylaluminum Species with a SixMembered Chair Conformation Al 2 C 2 N 2 Framework: A New Path to Geminal N/Al
Frustrated Lewis Pairs. Organometallics 31:4072–4075. https://doi.org/10.1021/om200967e
18. El-Hamdi M, Timoshkin AY (2019) Hydrogen Splitting by Pyramidalized 13–15 DonorAcceptor Cryptands: a Computational Study. J Comp Chem 40:1892–1901. https://doi.org/
10.1002/jcc.25845
19. Li Z, Guo J, Lu Y, Hu W, Dang Y, Wang ZX (2018) A Strategy for Developing MetalFree Hydrogenantion Catalysts: a DFT Proof-of-Principle Study. Dalton Trans 47:7709–
7714. https://doi.org/10.1039/C8DT01619D
20. Li W, Li C, Lyu Y (2019) A Computational Mechanistic Insight into H 2 Activation and
CO 2 Reduction over β-Diketiminato-ligand Group 13 Metal Complexes. J Catalysis 373:1–
12. https://doi.org/10.1016/j.jcat.2019.03.029
21. Lam J, Szkop KM, Mosaferi E, Stephan DW (2019) FLP Catalysis: Main Group Hydrogenations of Organic Unsaturated Substrates. Chem Soc Rev 48:3592–3612. https://doi.org/10.
1039/C8CS00277K
22. McCahill JSJ, Welch GC, Stephan DW (2007) Reactivity of ‘Frustrated Lewis Pairs’: ThreeComponent Reactions of Phosphines, a Borane, and Olefins. Angew Chem Int Ed 46:4968–
4971. https://doi.org/10.1002/anie.200701215
23. Knitsch R, Özgün T, Chen GQ, Kehr G, Erker G, Hansen MR, Eckert H (2019) Dihydrogen
Splitting by Intramolecular Borane-Phosphane Frustrated Lewis Pairs: A Comprehensive
Characterization Strategy Using Solid State NMR and DFT Calculations. ChemPhysChem
20:1837–1849. https://doi.org/10.1002/cphc.201900406
24. Whittell G, Balmond EI, Robertson AP, Patra SK, Haddow MF, Manners I (2010) Reaction
of Amine-Borane Adducts with Frustrated Lewis Pair Combinations of Group 14 Triflates
and Sterically Hindered Nitrogen Bases. Eur J Inorg Chem 2010:3967–3975. https://doi.org/
10.1002/ejic.201000515
25. Scott DJ, Phillip NA, Sapsford JS, Deacy AC, Fuchter MJ Ashley AE (2016) Versatile Catalytic Hydrogenation using a Simple Tin(IV) Lewis Acid. Angew Chem Int Ed
55:14738–14742. https://doi.org/10.1002/anie.201606639
26. Cooper RT, Sapsford JS, Turnell-Ritson RC, Hyon DH, White AJP, Ashley AE (2017)
Hydrogen Activation using a Novel Tribenzyltin Lewis Acid. Phil Trans R Soc A
375:20170008. https://doi.org/10.1098/rsta.2017.0008
27. Das S, Mondal S, Pati SK (2018) Mechanistic Insight into Hydrogen Activation by Frustrated
N/Sn Lewis Pairs. Chem Eur J 24:2575–2579. https://doi.org/10.1002/chem.201705861
28. Hounjet LJ, Bannwarth C, Garon CN, Caputo CB, Grimme S, Stephan DW (2013) Combinations of Ethers and B(C 6 F 5 ) 3 Function as Hydrogenation Catalysts. Angew Chem Int Ed
52:7492–7495. https://doi.org/10.1002/anie.201303166
29. 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
30. 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
31. Bannwarth C, Hansen A, Grimme S (2015) The Association of Two “Frustrated” Lewis Pairs
by State-of-the-Art Quantum Chemical Methods. Isr J Chem 55:235–242. https://doi.org/10.
1002/ijch.201400138
32. Bistoni G, Auer AA, Neese F (2017) Understanding the Role of Dispersion in Frustrated Lewis
Pairs and Classical Lewis Adducts: A Domain-Based Local Pair Natural Orbital Coupled
Cluster Study. Chem Eur J 23:865–873. https://doi.org/10.1002/chem.201604127