2 Frustrated Lewis Pair Catalyzed Asymmetric Reactions
85
37. Zhu X, Du H (2015) A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the
Synthesis of Cis-Vicinal Diamines. Org Lett 17:3106–3109. https://doi.org/10.1021/acs.org
lett.5b01380
38. Wei S, Feng X, Du H (2016) A Metal-Free Hydrogenation of 3-Substituted 2H-1,4Benzoxazines. Org Biomol Chem 14:8026–8029. https://doi.org/10.1039/C6OB01556E
39. Mahdi T, del Castillo JN, Stephan DW (2013) Metal-Free Hydrogenation of N-Based
Heterocycles. Organometallics 32:1971–1978. https://doi.org/10.1021/om4000727
40. Liu Y, Du H (2013) Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of
Pyridines. J Am Chem Soc 135:12968–12971. https://doi.org/10.1021/ja406761j
41. Wang W, Feng X, Du H (2016) Borane-Catalyzed Metal-Free Hydrogenation of 2,7Disubstituted 1,8-Naphthyridines. Org Biomol Chem 14:6683–6686. https://doi.org/10.1039/
C6OB01172A
42. Zhang Z, Du H (2015) A Highly cis-Selective and Enantioselective Metal-Free Hydrogenation
of 2,3-Disubstituted Quinoxalines. Angew Chem Int Ed 54:623–626. https://doi.org/10.1002/
anie.201409471
43. Zhang Z, Du H (2015) Cis-Selective and Highly Enantioselective Hydrogenation of 2,3,4Trisubstituted Quinolines. Org Lett 17:2816–2819. https://doi.org/10.1021/acs.orglett.5b0
1240
44. Zhang Z, Du H (2015) Enantioselective Metal-Free Hydrogenations of Disubstituted Quinolines. Org Lett 17:6266–6269. https://doi.org/10.1021/acs.orglett.5b03307
45. Han C, Zhang E, Feng X, Wang S, Du H (2018) B(C 6 F 5 ) 3 -Catalyzed Metal-Free Hydrogenations of 2-Quinolinecarboxylates. Tetrahedron Lett 59:1400–1403. https://doi.org/10.1016/j.
tetlet.2018.02.057
46. Li X, Tian J-J, Liu N, Tu X-S, Zeng N-N, Wang X-C (2019) Spiro-Bicyclic Bisborane Catalysts
for Metal-Free Chemoselective and Enantioselective Hydrogenation of Quinolines. Angew
Chem Int Ed 58:4664–4668. https://doi.org/10.1002/anie.201900907
47. Wang H, Fröhlich R, Kehr G, Erker G (2008) Heterolytic Dihydrogen Activation with the
1,8-Bis(diphenylphosphino)naphthalene/B(C 6 F 5 ) 3 Pair and Its Application for Metal-Free
Catalytic Hydrogenation of Silyl Enol Ethers. Chem Commun 5966–5968. https://doi.org/
10.1039/B813286K
48. Wei S, Du H (2014) A Highly Enantioselective Hydrogenation of Silyl Enol Ethers Catalyzed
by Chiral Frustrated Lewis Pairs. J Am Chem Soc 136:12261–12264. https://doi.org/10.1021/
ja507536n
49. Ren X, Li G, Wei S, Du H (2015) Facile Development of Chiral Alkenylboranes from Chiral
Diynes for Asymmetric Hydrogenation of Silyl Enol Ethers. Org Lett 17:990–993. https://doi.
org/10.1021/acs.orglett.5b00085
50. 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
51. 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
52. Gao B, Feng X, Meng W, Du H (2020) Asymmetric Hydrogenations of Ketones and Enones with
Chiral Lewis Base Derived Frustrated Lewis Pairs. Angew Chem Int Ed 59:4498–4504. https://
doi.org/10.1002/anie.201914568
53. Parks DJ, Piers WE (1996) Tris(pentafluorophenyl)boron-Catalyzed Hydrosilation of Aromatic
Aldehydes, Ketones, and Esters. J Am Chem Soc 118:9440–9441. https://doi.org/10.1021/ja9
61536g
54. Zhu X, Du H (2015) A Chiral Borane Catalyzed Asymmetric Hydrosilylation of Imines. Org
Biomol Chem 13:1013–1016. https://doi.org/10.1039/C4OB02419B
55. Ren X, Du H (2016) Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds. J Am Chem Soc 138:810–813. https://doi.org/10.
1021/jacs.5b13104
56. Süsse L, Hermeke J, Oestreich M (2016) The Asymmetric Piers Hydrosilylation. J Am Chem
Soc 138:6940−6943. https://doi.org/10.1021/jacs.6b03443
85
37. Zhu X, Du H (2015) A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the
Synthesis of Cis-Vicinal Diamines. Org Lett 17:3106–3109. https://doi.org/10.1021/acs.org
lett.5b01380
38. Wei S, Feng X, Du H (2016) A Metal-Free Hydrogenation of 3-Substituted 2H-1,4Benzoxazines. Org Biomol Chem 14:8026–8029. https://doi.org/10.1039/C6OB01556E
39. Mahdi T, del Castillo JN, Stephan DW (2013) Metal-Free Hydrogenation of N-Based
Heterocycles. Organometallics 32:1971–1978. https://doi.org/10.1021/om4000727
40. Liu Y, Du H (2013) Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of
Pyridines. J Am Chem Soc 135:12968–12971. https://doi.org/10.1021/ja406761j
41. Wang W, Feng X, Du H (2016) Borane-Catalyzed Metal-Free Hydrogenation of 2,7Disubstituted 1,8-Naphthyridines. Org Biomol Chem 14:6683–6686. https://doi.org/10.1039/
C6OB01172A
42. Zhang Z, Du H (2015) A Highly cis-Selective and Enantioselective Metal-Free Hydrogenation
of 2,3-Disubstituted Quinoxalines. Angew Chem Int Ed 54:623–626. https://doi.org/10.1002/
anie.201409471
43. Zhang Z, Du H (2015) Cis-Selective and Highly Enantioselective Hydrogenation of 2,3,4Trisubstituted Quinolines. Org Lett 17:2816–2819. https://doi.org/10.1021/acs.orglett.5b0
1240
44. Zhang Z, Du H (2015) Enantioselective Metal-Free Hydrogenations of Disubstituted Quinolines. Org Lett 17:6266–6269. https://doi.org/10.1021/acs.orglett.5b03307
45. Han C, Zhang E, Feng X, Wang S, Du H (2018) B(C 6 F 5 ) 3 -Catalyzed Metal-Free Hydrogenations of 2-Quinolinecarboxylates. Tetrahedron Lett 59:1400–1403. https://doi.org/10.1016/j.
tetlet.2018.02.057
46. Li X, Tian J-J, Liu N, Tu X-S, Zeng N-N, Wang X-C (2019) Spiro-Bicyclic Bisborane Catalysts
for Metal-Free Chemoselective and Enantioselective Hydrogenation of Quinolines. Angew
Chem Int Ed 58:4664–4668. https://doi.org/10.1002/anie.201900907
47. Wang H, Fröhlich R, Kehr G, Erker G (2008) Heterolytic Dihydrogen Activation with the
1,8-Bis(diphenylphosphino)naphthalene/B(C 6 F 5 ) 3 Pair and Its Application for Metal-Free
Catalytic Hydrogenation of Silyl Enol Ethers. Chem Commun 5966–5968. https://doi.org/
10.1039/B813286K
48. Wei S, Du H (2014) A Highly Enantioselective Hydrogenation of Silyl Enol Ethers Catalyzed
by Chiral Frustrated Lewis Pairs. J Am Chem Soc 136:12261–12264. https://doi.org/10.1021/
ja507536n
49. Ren X, Li G, Wei S, Du H (2015) Facile Development of Chiral Alkenylboranes from Chiral
Diynes for Asymmetric Hydrogenation of Silyl Enol Ethers. Org Lett 17:990–993. https://doi.
org/10.1021/acs.orglett.5b00085
50. 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
51. 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
52. Gao B, Feng X, Meng W, Du H (2020) Asymmetric Hydrogenations of Ketones and Enones with
Chiral Lewis Base Derived Frustrated Lewis Pairs. Angew Chem Int Ed 59:4498–4504. https://
doi.org/10.1002/anie.201914568
53. Parks DJ, Piers WE (1996) Tris(pentafluorophenyl)boron-Catalyzed Hydrosilation of Aromatic
Aldehydes, Ketones, and Esters. J Am Chem Soc 118:9440–9441. https://doi.org/10.1021/ja9
61536g
54. Zhu X, Du H (2015) A Chiral Borane Catalyzed Asymmetric Hydrosilylation of Imines. Org
Biomol Chem 13:1013–1016. https://doi.org/10.1039/C4OB02419B
55. Ren X, Du H (2016) Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of 1,2-Dicarbonyl Compounds. J Am Chem Soc 138:810–813. https://doi.org/10.
1021/jacs.5b13104
56. Süsse L, Hermeke J, Oestreich M (2016) The Asymmetric Piers Hydrosilylation. J Am Chem
Soc 138:6940−6943. https://doi.org/10.1021/jacs.6b03443