9 Frustrated Lewis Pairs Based on Transition Metals
353
85. Thai TT, Mérel DS, Poater A, Gaillard S, Renaud JL (2015) Highly Active Phosphine-Free
Bifunctional Iron Complex for Hydrogenation of Bicarbonate and Reductive Amination.
Chem Eur J 21:7066–7070. https://doi.org/10.1002/chem.201500720
86. Seck C, Mbaye MD, Coufourier S, Lator A, Lohier JF, Poater A, Ward TR, Gaillard S,
Renaud JL (2017) Alkylation of Ketones Catalyzed by Bifunctional Iron Complexes: From
Mechanistic Understanding to Application. ChemCatChem 9:4410–4416. https://doi.org/10.
1002/cctc.201701241
87. Lator A, Gaillard QG, Mérel DS, Lohier JF, Gaillard S, Poater A, Renaud JL (2019) RoomTemperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined
Iron (II) Complex Using Hydrogen. J Org Chem 84:6813–6829. https://doi.org/10.1021/acs.
joc.9b00581
88. Conley BL, Pennington-Boggio MK, Boz E, Williams TJ (2010) Discovery, Applications
and Catalytic Mechanisms of Shvo’s Catalyst. Chem Rev 110:2294–2312. https://doi.org/10.
1021/cr9003133
89. Klare HFT, Oestreich M, Ito J-I, Nishiyama H, Ohki Y, Tatsumi K (2011) Cooperative Catalytic
Activation of Si−H Bonds by a Polar Ru−S Bond: Regioselective Low-Temperature C−H
Silylation of Indoles Under Neutral Conditions by a Friedel−Crafts Mechanism. J Am Chem
Soc 133:3312–3315. https://doi.org/10.1021/ja111483r
90. Königs CDF, Klare HFT, Ohki Y, Tatsumi K, Oestreich M (2012) Base-Free Dehydrogenative
Coupling of Enolizable Carbonyl Compounds with Silanes. Org Lett 14:2842–2845. https://
doi.org/10.1021/ol301089r
91. Hermeke J, Klare HFT, Oestreich M (2014) Direct Catalytic Access to N-Silylated Enamines
from Enolizable Imines and Hydrosilanes by Base-Free Dehydrogenative Si—N Coupling.
Chem Eur J 20:9250–9254. https://doi.org/10.1002/chem.201402866
92. Königs CDF, Müller MF, Aiguabella N, Klare HFT, Oestreich M (2013) Catalytic Dehydrogenative Si–N Coupling of Pyrroles, Indoles, Carbazoles as well as Anilines with Hydrosilanes
without Added Base. Chem Commun 49:1506–1508. https://doi.org/10.1039/C3CC38900F
93. Königs CDF, Klare HFT, Oestreich M (2013) Catalytic 1,4-Selective Hydrosilylation of
Pyridines and Benzannulated Congeners. Angew Chem Int Ed 52:10076–10079. https://doi.
org/10.1002/anie.201305028
94. Metsänen TT, Oestreich M (2015) Temperature-Dependent Chemoselective Hydrosilylation
of Carbon Dioxide to Formaldehyde or Methanol Oxidation State. Organometallics 34:543–
546. https://doi.org/10.1021/om501279a
95. Stahl T, Klare HFT, Oestreich M (2013) C(sp3)–F bond Activation of CF 3 -Substituted
Anilines with Catalytically Generated Silicon Cations: Spectroscopic Evidence for a HydrideBridged Ru–S Dimer in the Catalytic Cycle. J Am Chem Soc 135:1248–1251. https://doi.org/
10.1021/ja311398j
96. Bähr S, Oestreich M (2017) Hidden Enantioselective Hydrogenation of N-Silyl Enamines
and Silyl Enol Ethers in Net C N and C O Hydrosilylations Catalyzed by Ru−S Complexes
with One Monodentate Chiral Phosphine Ligand. Organometallics 36:935–943. https://doi.
org/10.1021/acs.organomet.7b00030
97. Webbolt S, Maji MS, Irran E, Oestreich M (2017) A Tethered Ru–S Complex with an Axial
Chiral Thiolate Ligand for Cooperative Si–H Bond Activation: Application to Enantioselective
Imine Reduction. Chem Eur J 23:6213–6219. https://doi.org/10.1002/chem.201700304
98. Stahl T, Hrobárik P, Königs CDF, Ohki Y, Tatsumi K, Kemper S, Kaupp M, Klare HFT,
Oestreich M (2015) Mechanism of the Cooperative Si–H Bond Activation at Ru–S Bonds.
Chem Sci 6:4324–4334. https://doi.org/10.1039/c5sc01035g
99. Ochi N, Matsumoto T, Dei T, Nakao Y, Sato H, Tatsumi K, Sakaki S (2015) Heterolytic
Activation of Dihydrogen Molecule by Hydroxo-/Sulfido-Bridged Ruthenium−Germanium
Dinuclear Complex. Theor Insights Inorg Chem 54:576–585. https://doi.org/10.1021/ic5
02463y
100. Matsumoto T, Nakaya Y, Itakura N, Tatsumi K (2008) A Functional Hydrogenase Model:
Reversible Interconversion of H 2 and H 2 O by a Hydroxo/Sulfido-Bridged Dinuclear
Ruthenium−Germanium Complex. J Am Chem Soc 130:2458–2459. https://doi.org/10.1021/
ja711325f
353
85. Thai TT, Mérel DS, Poater A, Gaillard S, Renaud JL (2015) Highly Active Phosphine-Free
Bifunctional Iron Complex for Hydrogenation of Bicarbonate and Reductive Amination.
Chem Eur J 21:7066–7070. https://doi.org/10.1002/chem.201500720
86. Seck C, Mbaye MD, Coufourier S, Lator A, Lohier JF, Poater A, Ward TR, Gaillard S,
Renaud JL (2017) Alkylation of Ketones Catalyzed by Bifunctional Iron Complexes: From
Mechanistic Understanding to Application. ChemCatChem 9:4410–4416. https://doi.org/10.
1002/cctc.201701241
87. Lator A, Gaillard QG, Mérel DS, Lohier JF, Gaillard S, Poater A, Renaud JL (2019) RoomTemperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined
Iron (II) Complex Using Hydrogen. J Org Chem 84:6813–6829. https://doi.org/10.1021/acs.
joc.9b00581
88. Conley BL, Pennington-Boggio MK, Boz E, Williams TJ (2010) Discovery, Applications
and Catalytic Mechanisms of Shvo’s Catalyst. Chem Rev 110:2294–2312. https://doi.org/10.
1021/cr9003133
89. Klare HFT, Oestreich M, Ito J-I, Nishiyama H, Ohki Y, Tatsumi K (2011) Cooperative Catalytic
Activation of Si−H Bonds by a Polar Ru−S Bond: Regioselective Low-Temperature C−H
Silylation of Indoles Under Neutral Conditions by a Friedel−Crafts Mechanism. J Am Chem
Soc 133:3312–3315. https://doi.org/10.1021/ja111483r
90. Königs CDF, Klare HFT, Ohki Y, Tatsumi K, Oestreich M (2012) Base-Free Dehydrogenative
Coupling of Enolizable Carbonyl Compounds with Silanes. Org Lett 14:2842–2845. https://
doi.org/10.1021/ol301089r
91. Hermeke J, Klare HFT, Oestreich M (2014) Direct Catalytic Access to N-Silylated Enamines
from Enolizable Imines and Hydrosilanes by Base-Free Dehydrogenative Si—N Coupling.
Chem Eur J 20:9250–9254. https://doi.org/10.1002/chem.201402866
92. Königs CDF, Müller MF, Aiguabella N, Klare HFT, Oestreich M (2013) Catalytic Dehydrogenative Si–N Coupling of Pyrroles, Indoles, Carbazoles as well as Anilines with Hydrosilanes
without Added Base. Chem Commun 49:1506–1508. https://doi.org/10.1039/C3CC38900F
93. Königs CDF, Klare HFT, Oestreich M (2013) Catalytic 1,4-Selective Hydrosilylation of
Pyridines and Benzannulated Congeners. Angew Chem Int Ed 52:10076–10079. https://doi.
org/10.1002/anie.201305028
94. Metsänen TT, Oestreich M (2015) Temperature-Dependent Chemoselective Hydrosilylation
of Carbon Dioxide to Formaldehyde or Methanol Oxidation State. Organometallics 34:543–
546. https://doi.org/10.1021/om501279a
95. Stahl T, Klare HFT, Oestreich M (2013) C(sp3)–F bond Activation of CF 3 -Substituted
Anilines with Catalytically Generated Silicon Cations: Spectroscopic Evidence for a HydrideBridged Ru–S Dimer in the Catalytic Cycle. J Am Chem Soc 135:1248–1251. https://doi.org/
10.1021/ja311398j
96. Bähr S, Oestreich M (2017) Hidden Enantioselective Hydrogenation of N-Silyl Enamines
and Silyl Enol Ethers in Net C N and C O Hydrosilylations Catalyzed by Ru−S Complexes
with One Monodentate Chiral Phosphine Ligand. Organometallics 36:935–943. https://doi.
org/10.1021/acs.organomet.7b00030
97. Webbolt S, Maji MS, Irran E, Oestreich M (2017) A Tethered Ru–S Complex with an Axial
Chiral Thiolate Ligand for Cooperative Si–H Bond Activation: Application to Enantioselective
Imine Reduction. Chem Eur J 23:6213–6219. https://doi.org/10.1002/chem.201700304
98. Stahl T, Hrobárik P, Königs CDF, Ohki Y, Tatsumi K, Kemper S, Kaupp M, Klare HFT,
Oestreich M (2015) Mechanism of the Cooperative Si–H Bond Activation at Ru–S Bonds.
Chem Sci 6:4324–4334. https://doi.org/10.1039/c5sc01035g
99. Ochi N, Matsumoto T, Dei T, Nakao Y, Sato H, Tatsumi K, Sakaki S (2015) Heterolytic
Activation of Dihydrogen Molecule by Hydroxo-/Sulfido-Bridged Ruthenium−Germanium
Dinuclear Complex. Theor Insights Inorg Chem 54:576–585. https://doi.org/10.1021/ic5
02463y
100. Matsumoto T, Nakaya Y, Itakura N, Tatsumi K (2008) A Functional Hydrogenase Model:
Reversible Interconversion of H 2 and H 2 O by a Hydroxo/Sulfido-Bridged Dinuclear
Ruthenium−Germanium Complex. J Am Chem Soc 130:2458–2459. https://doi.org/10.1021/
ja711325f