1 Frustrated Lewis Pair Catalysis: An Introduction
23
52. Chernichenko K, Madarász Á, Pápai I, Nieger M, Leskelä M, Repo T (2013) A FrustratedLewis-Pair Approach to Catalytic Reduction of Alkynes to cis-Alkenes. Nature Chem 5:718–
723. https://doi.org/10.1038/nchem.1693
53. Chernichenko K, Kotai B, Nieger M, Heikkinen S, Papai I, Repo T (2017) Replacing
C 6 F 5 Groups with Cl and H Atoms in Frustrated Lewis Pairs: H 2 Additions and Catalytic
Hydrogenations. Dalton Trans 46(7):2263–2269. https://doi.org/10.1039/c6dt04649e
54. Liu YB, Hu LR, Chen H, Du HF (2015) An Alkene-Promoted Borane-Catalyzed Highly
Stereoselective Hydrogenation of Alkynes to give Z- and E-Alkenes. Chem Eur J 21(8):3495–
3501. https://doi.org/10.1002/chem.201405388
55. Scott DJ, Fuchter MJ, Ashley AE (2014b) Metal-Free Hydrogenation Catalyzed by an AirStable Borane: Use of Solvent as a Frustrated Lewis Base. Angew Chem Int Ed 53(38):10218–
10222. https://doi.org/10.1002/anie.201405531
56. Mahdi T, Stephan DW (2015a) Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes. Angew Chem Int Ed
54(29):8511–8514. https://doi.org/10.1002/anie.201503087
57. Eros G, Nagy K, Mehdi H, Papai I, Nagy P, Kiraly P, Tarkanyi G, Soós T (2012) Catalytic
Hydrogenation with Frustrated Lewis Pairs: Selectivity Achieved by Size-Exclusion Design
of Lewis Acids. Chem Eur J 18(2):574–585. https://doi.org/10.1002/chem.201102438
58. Bakos M, Gyomore A, Domjan A, Soós T (2017) Auto-Tandem Catalysis with Frustrated
Lewis Pairs for Reductive Etherification of Aldehydes and Ketones. Angew Chem Int Ed
56:5217–5221. https://doi.org/10.1002/anie.201700231
59. Gyömöre Á, Bakos M, Földes T, Pápai I, Domján A, Soós T (2015) Moisture-Tolerant Frustrated Lewis Pair Catalyst for Hydrogenation of Aldehydes and Ketones. ACS Catalysis
5:5366–5372. https://doi.org/10.1021/acscatal.5b01299
60. Cooper RT, Sapsford JS, Turnell-Ritson RC, Hyon DH, White AJP, Ashley AE (2017)
Hydrogen Activation Using a Novel Tribenzyltin Lewis Acid. Phil Trans A 375: 2101. ARTN
20170008. https://doi.org/10.1098/rsta.2017.0008
61. Scott DJ, Phillips 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
62. Tussing S, Greb L, Tamke S, Schirmer B, Muhle-Goll C, Luy B, Paradies J (2015) Autoinduced Catalysis and Inverse Equilibrium Isotope Effect in the Frustrated Lewis Pair Catalyzed
Hydrogenation of Imines. Chem Eur J 21(22):8056–8059. https://doi.org/10.1002/chem.201
500805
63. Tussing S, Kaupmees K, Paradies J (2016) Structure-Reactivity Relationship in the Frustrated
Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines. Chem Eur J 22(22):7422–7426. https://
doi.org/10.1002/chem.201600716
64. Nicasio JA, Steinberg S, Inés B, Alcarazo M (2013) Tuning the Lewis Acidity of Boranes
in Frustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor
Alkenes. Chem Eur J 19(33):11016–11020. https://doi.org/10.1002/chem.201301158
65. Sumerin V, Schulz F, Atsumi M, Wang C, Nieger M, Leskelä M, Repo T, Pyykkö P, Rieger B
(2008) Molecular Tweezers for Hydrogen: Synthesis, Characterization, and Reactivity. J Am
Chem Soc 130(43):14117–14118. https://doi.org/10.1021/Ja806627s
66. Feldmann A, Kehr G, Daniliuc CG, Muck-Lichtenfeld C, Erker G (2015) Functionalization of
Intramolecular Frustrated Lewis Pairs by 1,1-Carboboration with Conjugated Enynes. Chem
Eur J 21(35):12456–12464. https://doi.org/10.1002/chem.201502278
67. Rosorius C, Moricke J, Wibbeling B, McQuilken AC, Warren TH, Daniliuc CG, Kehr G,
Erker G (2016) Frustrated Lewis Pair Chemistry Derived from Bulky Allenyl and Propargyl
Phosphanes. Chem Eur J 22(3):1103–1113. https://doi.org/10.1002/chem.201502493
68. Korte LA, Blomeyer S, Heidemeyer S, Nissen JH, Mix A, Neumann B, Stammler HG, Mitzel
NW (2016) Intramolecular Lewis Pairs with Two Acid Sites - Reactivity Differences Between
P- and N-Based Systems. Dalton Trans 45(43):17319–17328. https://doi.org/10.1039/c6dt03
490j
23
52. Chernichenko K, Madarász Á, Pápai I, Nieger M, Leskelä M, Repo T (2013) A FrustratedLewis-Pair Approach to Catalytic Reduction of Alkynes to cis-Alkenes. Nature Chem 5:718–
723. https://doi.org/10.1038/nchem.1693
53. Chernichenko K, Kotai B, Nieger M, Heikkinen S, Papai I, Repo T (2017) Replacing
C 6 F 5 Groups with Cl and H Atoms in Frustrated Lewis Pairs: H 2 Additions and Catalytic
Hydrogenations. Dalton Trans 46(7):2263–2269. https://doi.org/10.1039/c6dt04649e
54. Liu YB, Hu LR, Chen H, Du HF (2015) An Alkene-Promoted Borane-Catalyzed Highly
Stereoselective Hydrogenation of Alkynes to give Z- and E-Alkenes. Chem Eur J 21(8):3495–
3501. https://doi.org/10.1002/chem.201405388
55. Scott DJ, Fuchter MJ, Ashley AE (2014b) Metal-Free Hydrogenation Catalyzed by an AirStable Borane: Use of Solvent as a Frustrated Lewis Base. Angew Chem Int Ed 53(38):10218–
10222. https://doi.org/10.1002/anie.201405531
56. Mahdi T, Stephan DW (2015a) Facile Protocol for Catalytic Frustrated Lewis Pair Hydrogenation and Reductive Deoxygenation of Ketones and Aldehydes. Angew Chem Int Ed
54(29):8511–8514. https://doi.org/10.1002/anie.201503087
57. Eros G, Nagy K, Mehdi H, Papai I, Nagy P, Kiraly P, Tarkanyi G, Soós T (2012) Catalytic
Hydrogenation with Frustrated Lewis Pairs: Selectivity Achieved by Size-Exclusion Design
of Lewis Acids. Chem Eur J 18(2):574–585. https://doi.org/10.1002/chem.201102438
58. Bakos M, Gyomore A, Domjan A, Soós T (2017) Auto-Tandem Catalysis with Frustrated
Lewis Pairs for Reductive Etherification of Aldehydes and Ketones. Angew Chem Int Ed
56:5217–5221. https://doi.org/10.1002/anie.201700231
59. Gyömöre Á, Bakos M, Földes T, Pápai I, Domján A, Soós T (2015) Moisture-Tolerant Frustrated Lewis Pair Catalyst for Hydrogenation of Aldehydes and Ketones. ACS Catalysis
5:5366–5372. https://doi.org/10.1021/acscatal.5b01299
60. Cooper RT, Sapsford JS, Turnell-Ritson RC, Hyon DH, White AJP, Ashley AE (2017)
Hydrogen Activation Using a Novel Tribenzyltin Lewis Acid. Phil Trans A 375: 2101. ARTN
20170008. https://doi.org/10.1098/rsta.2017.0008
61. Scott DJ, Phillips 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
62. Tussing S, Greb L, Tamke S, Schirmer B, Muhle-Goll C, Luy B, Paradies J (2015) Autoinduced Catalysis and Inverse Equilibrium Isotope Effect in the Frustrated Lewis Pair Catalyzed
Hydrogenation of Imines. Chem Eur J 21(22):8056–8059. https://doi.org/10.1002/chem.201
500805
63. Tussing S, Kaupmees K, Paradies J (2016) Structure-Reactivity Relationship in the Frustrated
Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines. Chem Eur J 22(22):7422–7426. https://
doi.org/10.1002/chem.201600716
64. Nicasio JA, Steinberg S, Inés B, Alcarazo M (2013) Tuning the Lewis Acidity of Boranes
in Frustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor
Alkenes. Chem Eur J 19(33):11016–11020. https://doi.org/10.1002/chem.201301158
65. Sumerin V, Schulz F, Atsumi M, Wang C, Nieger M, Leskelä M, Repo T, Pyykkö P, Rieger B
(2008) Molecular Tweezers for Hydrogen: Synthesis, Characterization, and Reactivity. J Am
Chem Soc 130(43):14117–14118. https://doi.org/10.1021/Ja806627s
66. Feldmann A, Kehr G, Daniliuc CG, Muck-Lichtenfeld C, Erker G (2015) Functionalization of
Intramolecular Frustrated Lewis Pairs by 1,1-Carboboration with Conjugated Enynes. Chem
Eur J 21(35):12456–12464. https://doi.org/10.1002/chem.201502278
67. Rosorius C, Moricke J, Wibbeling B, McQuilken AC, Warren TH, Daniliuc CG, Kehr G,
Erker G (2016) Frustrated Lewis Pair Chemistry Derived from Bulky Allenyl and Propargyl
Phosphanes. Chem Eur J 22(3):1103–1113. https://doi.org/10.1002/chem.201502493
68. Korte LA, Blomeyer S, Heidemeyer S, Nissen JH, Mix A, Neumann B, Stammler HG, Mitzel
NW (2016) Intramolecular Lewis Pairs with Two Acid Sites - Reactivity Differences Between
P- and N-Based Systems. Dalton Trans 45(43):17319–17328. https://doi.org/10.1039/c6dt03
490j