22
D. W. Stephan
33. Jian ZB, Krupski S, Skoch K, Kehr G, Daniliuc CG, Cisarova I, Stepnicka P, Erker G (2017)
Phosphine Borane Frustrated Lewis Pairs Derived from a 1,1‘-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis. Organometallics 36(15):2940–2946. https://
doi.org/10.1021/acs.organomet.7b00363
34. Eros G, Mehdi H, Papai I, Rokob TA, Kiraly P, Tarkanyi G, Soós T (2010) Expanding the
Scope of Metal-Free Catalytic Hydrogenation Through Frustrated Lewis Pair Design. Angew
Chem Int Ed 49(37):6559–6563. https://doi.org/10.1002/anie.201001518
35. Reddy JS, Xu BH, Mahdi T, Fröhlich R, Kehr G, Stephan DW, Erker G (2012) AlkenylboraneDerived Frustrated Lewis Pairs: Metal-Free Catalytic Hydrogenation Reactions of ElectronDeficient Alkenes. Organometallics 31(15):5638–5649. https://doi.org/10.1021/Om3006068
36. Khan I, Manzotti M, Tizzard GJ, Coles SJ, Melen RL, Morrill LC (2017) Frustrated Lewis
Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita–Baylis–Hillman Adducts and Sequential
Organo-FLP Catalysis. ACS Catalysis 7(11):7748–7752. https://doi.org/10.1021/acscatal.
7b03077
37. Geier SJ, Chase PA, Stephan DW (2010) Metal-Free Reductions of N-Heterocycles via Lewis
Acid Catalyzed Hydrogenation. Chem Commun 46(27):4884–4886. https://doi.org/10.1039/
C0cc00719f
38. Mahdi T, del Castillo JN, Stephan DW (2013) Metal-Free Hydrogenation of N-Based
Heterocycles. Organometallics 32(6):1971–1978. https://doi.org/10.1021/Om4000727
39. Liu YB, Du HF (2013) Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation
of Pyridines. J Am Chem Soc 135(35):12968–12971. https://doi.org/10.1021/ja406761j
40. Wang W, Feng XQ, Du HF (2016) Borane-Catalyzed Metal-Free Hydrogenation of 2,7Disubstituted 1,8-Naphthyridines. Org Biomol Chem 14(28):6683–6686. https://doi.org/10.
1039/C6OB01172A
41. Wei S, Feng X, Du H (2016) A Metal-Free Hydrogenation of 3-Substituted 2H–1,4Benzoxazines. Org Biomol Chem 14(34):8026–8029. https://doi.org/10.1039/c6ob01556e
42. Zhang ZH, Du HF (2015) A Highly cis-Selective and Enantioselective Metal-Free Hydrogenation of 2,3-Disubstituted Quinoxalines. Angew Chem Int Ed 54(2):623–626. https://doi.
org/10.1002/anie.201409471
43. Wang W, Meng W, Du H (2015) B(C 6 F 5 ) 3 -Catalyzed Metal-Free Hydrogenation of 3,6Diarylpyridazines. Dalton Trans 45:5945–5948. https://doi.org/10.1039/C5DT03872C
44. Greb L, Oña-Burgos P, Schirmer B, Grimme S, Stephan DW, Paradies J (2012) Metal-Free
Catalytic Olefin Hydrogenations: Low Temperature H 2 -Activation by Frustrated Lewis Pairs.
Angew Chem Int Ed 51:10164–10168. https://doi.org/10.1002/anie.201204007
45. 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(29):7492–7495. https://doi.org/10.1002/anie.201303166
46. Segawa Y, Stephan DW (2012) Metal-Free Hydrogenation Catalysis of Polycyclic Aromatic
Hydrocarbons. Chem Commun 48(98):11963–11965. https://doi.org/10.1039/c2cc37190a
47. Tamke S, Daniliuc CG, Paradies J (2014) Frustrated Lewis Pair Catalyzed Hydrosilylation
and Hydrosilane Mediated Hydrogenation of Fulvenes. Org Biomol Chem 12(45):9139–9144.
https://doi.org/10.1039/c4ob01346h
48. Elmer LM, Kehr G, Daniliuc CG, Siedow M, Eckert H, Tesch M, Studer A, Williams K, Warren
TH, Erker G (2017) The Chemistry of a Non-Interacting Vicinal Frustrated Phosphane/Borane
Lewis Pair. Chem Eur J 23(25):6056–6068. https://doi.org/10.1002/chem.201603954
49. Wang Y, Chen W, Lu Z, Li ZH, Wang H (2013) Metal-Free HB(C 6 F 5 ) 2 -Catalyzed Hydrogenation of Unfunctionalized Olefins and Mechanism Study of Borane-Mediated σ-Bond
Metathesis. Angew Chem Int Ed 52:7496–7499. https://doi.org/10.1002/anie.201303500
50. Mahdi T, Heiden ZM, Grimme S, Stephan DW (2012) Metal-Free Aromatic Hydrogenation:
Aniline to Cyclohexyl-Amine Derivatives. J Am Chem Soc 134(9):4088–4091. https://doi.
org/10.1021/ja300228a
51. Li G, Liu YB, Du HF (2015) B(C 6 F 5 ) 3 -Catalyzed Metal-Free Hydrogenation of Naphthylamines. Org Biomol Chem 13(10):2875–2878. https://doi.org/10.1039/c5ob00009b
D. W. Stephan
33. Jian ZB, Krupski S, Skoch K, Kehr G, Daniliuc CG, Cisarova I, Stepnicka P, Erker G (2017)
Phosphine Borane Frustrated Lewis Pairs Derived from a 1,1‘-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis. Organometallics 36(15):2940–2946. https://
doi.org/10.1021/acs.organomet.7b00363
34. Eros G, Mehdi H, Papai I, Rokob TA, Kiraly P, Tarkanyi G, Soós T (2010) Expanding the
Scope of Metal-Free Catalytic Hydrogenation Through Frustrated Lewis Pair Design. Angew
Chem Int Ed 49(37):6559–6563. https://doi.org/10.1002/anie.201001518
35. Reddy JS, Xu BH, Mahdi T, Fröhlich R, Kehr G, Stephan DW, Erker G (2012) AlkenylboraneDerived Frustrated Lewis Pairs: Metal-Free Catalytic Hydrogenation Reactions of ElectronDeficient Alkenes. Organometallics 31(15):5638–5649. https://doi.org/10.1021/Om3006068
36. Khan I, Manzotti M, Tizzard GJ, Coles SJ, Melen RL, Morrill LC (2017) Frustrated Lewis
Pair (FLP)-Catalyzed Hydrogenation of Aza-Morita–Baylis–Hillman Adducts and Sequential
Organo-FLP Catalysis. ACS Catalysis 7(11):7748–7752. https://doi.org/10.1021/acscatal.
7b03077
37. Geier SJ, Chase PA, Stephan DW (2010) Metal-Free Reductions of N-Heterocycles via Lewis
Acid Catalyzed Hydrogenation. Chem Commun 46(27):4884–4886. https://doi.org/10.1039/
C0cc00719f
38. Mahdi T, del Castillo JN, Stephan DW (2013) Metal-Free Hydrogenation of N-Based
Heterocycles. Organometallics 32(6):1971–1978. https://doi.org/10.1021/Om4000727
39. Liu YB, Du HF (2013) Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation
of Pyridines. J Am Chem Soc 135(35):12968–12971. https://doi.org/10.1021/ja406761j
40. Wang W, Feng XQ, Du HF (2016) Borane-Catalyzed Metal-Free Hydrogenation of 2,7Disubstituted 1,8-Naphthyridines. Org Biomol Chem 14(28):6683–6686. https://doi.org/10.
1039/C6OB01172A
41. Wei S, Feng X, Du H (2016) A Metal-Free Hydrogenation of 3-Substituted 2H–1,4Benzoxazines. Org Biomol Chem 14(34):8026–8029. https://doi.org/10.1039/c6ob01556e
42. Zhang ZH, Du HF (2015) A Highly cis-Selective and Enantioselective Metal-Free Hydrogenation of 2,3-Disubstituted Quinoxalines. Angew Chem Int Ed 54(2):623–626. https://doi.
org/10.1002/anie.201409471
43. Wang W, Meng W, Du H (2015) B(C 6 F 5 ) 3 -Catalyzed Metal-Free Hydrogenation of 3,6Diarylpyridazines. Dalton Trans 45:5945–5948. https://doi.org/10.1039/C5DT03872C
44. Greb L, Oña-Burgos P, Schirmer B, Grimme S, Stephan DW, Paradies J (2012) Metal-Free
Catalytic Olefin Hydrogenations: Low Temperature H 2 -Activation by Frustrated Lewis Pairs.
Angew Chem Int Ed 51:10164–10168. https://doi.org/10.1002/anie.201204007
45. 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(29):7492–7495. https://doi.org/10.1002/anie.201303166
46. Segawa Y, Stephan DW (2012) Metal-Free Hydrogenation Catalysis of Polycyclic Aromatic
Hydrocarbons. Chem Commun 48(98):11963–11965. https://doi.org/10.1039/c2cc37190a
47. Tamke S, Daniliuc CG, Paradies J (2014) Frustrated Lewis Pair Catalyzed Hydrosilylation
and Hydrosilane Mediated Hydrogenation of Fulvenes. Org Biomol Chem 12(45):9139–9144.
https://doi.org/10.1039/c4ob01346h
48. Elmer LM, Kehr G, Daniliuc CG, Siedow M, Eckert H, Tesch M, Studer A, Williams K, Warren
TH, Erker G (2017) The Chemistry of a Non-Interacting Vicinal Frustrated Phosphane/Borane
Lewis Pair. Chem Eur J 23(25):6056–6068. https://doi.org/10.1002/chem.201603954
49. Wang Y, Chen W, Lu Z, Li ZH, Wang H (2013) Metal-Free HB(C 6 F 5 ) 2 -Catalyzed Hydrogenation of Unfunctionalized Olefins and Mechanism Study of Borane-Mediated σ-Bond
Metathesis. Angew Chem Int Ed 52:7496–7499. https://doi.org/10.1002/anie.201303500
50. Mahdi T, Heiden ZM, Grimme S, Stephan DW (2012) Metal-Free Aromatic Hydrogenation:
Aniline to Cyclohexyl-Amine Derivatives. J Am Chem Soc 134(9):4088–4091. https://doi.
org/10.1021/ja300228a
51. Li G, Liu YB, Du HF (2015) B(C 6 F 5 ) 3 -Catalyzed Metal-Free Hydrogenation of Naphthylamines. Org Biomol Chem 13(10):2875–2878. https://doi.org/10.1039/c5ob00009b