122
4 Theoretical View of Rh-Catalyzed C–H Functionalization …
71. Hachiya H, Hirano K, Satoh T, Miura M (2010) Nickel-catalyzed direct C–H arylation and
alkenylation of heteroarenes with organosilicon reagents. Angew Chem Int Ed 49:2202–2205
72. Komiyama T, Minami Y, Hiyama T (2017) Recent advances in transition-metal-catalyzed
synthetic transformations of organosilicon reagents. ACS Catal 7:631–651
73. Li C, Dou J, Cao J, Li Z, Chen W, Zhu Q, Zhu C (2013) A novel chelating organosilicone
resin bearing long chain imidazolyl ligands: Preparation, characterization, and adsorption
properties. J Organomet Chem 727:37–43
74. Nakao Y, Hiyama T (2011) Silicon-based cross-coupling reaction: an environmentally benign
version. Chem Soc Rev 40:4893–4901
75. Prakash GKS, Yudin AK (1997) Perfluoroalkylation with organosilicon reagents. Chem Rev
97:757–786
76. Rendón-Nava D, Vásquez-Pérez JM, Sandoval-Chávez CI, Alvarez-Hernández A, MendozaEspinosa D (2020) Synthesis of multinuclear Rh(I) complexes bearing triazolylidenes and
their application in C-C and C–Si bond forming reactions. Organometallics 39:3961–3971
77. Sore HF, Galloway WRJD, Spring DR (2012) Palladium-catalysed cross-coupling of
organosilicon reagents. Chem Soc Rev 41:1845–1866
78. Cheng C, Hartwig JF (2015) Catalytic Silylation of Unactivated C–H Bonds. Chem Rev
115:8946–8975
79. Cheng C, Simmons EM, Hartwig JF (2013) Iridium-catalyzed, diastereoselective dehydrogenative silylation of terminal alkenes with (TMSO) 2 MeSiH. Angew Chem Int Ed
52:8984–8989
80. Elsby MR, Johnson SA (2017) Nickel-catalyzed C–H silylation of arenes with vinylsilanes:
rapid and reversible β-Si elimination. J Am Chem Soc 139:9401–9407
81. Esteruelas MA, Martínez A, Oliván M, Oñate E (2020) Kinetic analysis and sequencing of
Si–H and C–H bond activation reactions: direct silylation of arenes catalyzed by an iridiumpolyhydride. J Am Chem Soc 142:19119–19131
82. Gu Y, Shen Y, Zarate C, Martin R (2019) A Mild and direct site-selective sp2 C–H silylation
of (poly)azines. J Am Chem Soc 141:127–132
83. Kakiuchi F, Igi K, Matsumoto M, Hayamizu T, Chatani N, Murai S (2002) A new chelationassistance mode for a ruthenium-catalyzed silylation at the C–H bond in aromatic ring with
hydrosilanes. Chem Lett 31:396–397
84. Kakiuchi F, Matsumoto M, Tsuchiya K, Igi K, Hayamizu T, Chatani N, Murai S (2003) The
ruthenium-catalyzed silylation of aromatic C–H bonds with triethylsilane. J Organomet Chem
686:134–144
85. Kakiuchi F, Tsuchiya K, Matsumoto M, Mizushima E, Chatani N (2004) Ru3(CO)12Catalyzed silylation of benzylic C−H bonds in arylpyridines and arylpyrazoles with
hydrosilanes via C − H bond cleavage. J Am Chem Soc 126:12792–12793
86. Karmel C, Chen Z, Hartwig JF (2019) Iridium-catalyzed silylation of C–H bonds in unactivated arenes: a sterically encumbered phenanthroline ligand accelerates catalysis. J Am Chem
Soc 141:7063–7072
87. Karmel C, Hartwig JF (2020) Mechanism of the iridium-catalyzed silylation of aromatic C–H
bonds. J Am Chem Soc 142:10494–10505
88. Karmel C, Rubel CZ, Kharitonova EV, Hartwig JF (2020) Iridium-catalyzed silylation of
five-membered heteroarenes: high sterically derived selectivity from a pyridyl-imidazoline
ligand. Angew Chem Int Ed 59:6074–6081
89. Ka´ zmierczak J, Kuci´ nski K, Lewandowski D, Hreczycho G (2019) Ru-Catalyzed dehydrogenative silylation of POSS-silanols with hydrosilanes: its introduction to one-pot synthesis.
Inorg Chem 58:1201–1207
90. Oyamada J, Nishiura M, Hou Z (2011) Scandium-catalyzed silylation of aromatic C–H bonds.
Angew Chem Int Ed 50:10720–10723
91. Richter SC, Oestreich M (2020) Emerging strategies for C–H silylation. Trends Chem 2:13–27
92. Saiki T, Nishio Y, Ishiyama T, Miyaura N (2006) Improvements of efficiency and regioselectivity in the iridium(i)-catalyzed aromatic CH silylation of arenes with fluorodisilanes.
Organometallics 25:6068–6073
4 Theoretical View of Rh-Catalyzed C–H Functionalization …
71. Hachiya H, Hirano K, Satoh T, Miura M (2010) Nickel-catalyzed direct C–H arylation and
alkenylation of heteroarenes with organosilicon reagents. Angew Chem Int Ed 49:2202–2205
72. Komiyama T, Minami Y, Hiyama T (2017) Recent advances in transition-metal-catalyzed
synthetic transformations of organosilicon reagents. ACS Catal 7:631–651
73. Li C, Dou J, Cao J, Li Z, Chen W, Zhu Q, Zhu C (2013) A novel chelating organosilicone
resin bearing long chain imidazolyl ligands: Preparation, characterization, and adsorption
properties. J Organomet Chem 727:37–43
74. Nakao Y, Hiyama T (2011) Silicon-based cross-coupling reaction: an environmentally benign
version. Chem Soc Rev 40:4893–4901
75. Prakash GKS, Yudin AK (1997) Perfluoroalkylation with organosilicon reagents. Chem Rev
97:757–786
76. Rendón-Nava D, Vásquez-Pérez JM, Sandoval-Chávez CI, Alvarez-Hernández A, MendozaEspinosa D (2020) Synthesis of multinuclear Rh(I) complexes bearing triazolylidenes and
their application in C-C and C–Si bond forming reactions. Organometallics 39:3961–3971
77. Sore HF, Galloway WRJD, Spring DR (2012) Palladium-catalysed cross-coupling of
organosilicon reagents. Chem Soc Rev 41:1845–1866
78. Cheng C, Hartwig JF (2015) Catalytic Silylation of Unactivated C–H Bonds. Chem Rev
115:8946–8975
79. Cheng C, Simmons EM, Hartwig JF (2013) Iridium-catalyzed, diastereoselective dehydrogenative silylation of terminal alkenes with (TMSO) 2 MeSiH. Angew Chem Int Ed
52:8984–8989
80. Elsby MR, Johnson SA (2017) Nickel-catalyzed C–H silylation of arenes with vinylsilanes:
rapid and reversible β-Si elimination. J Am Chem Soc 139:9401–9407
81. Esteruelas MA, Martínez A, Oliván M, Oñate E (2020) Kinetic analysis and sequencing of
Si–H and C–H bond activation reactions: direct silylation of arenes catalyzed by an iridiumpolyhydride. J Am Chem Soc 142:19119–19131
82. Gu Y, Shen Y, Zarate C, Martin R (2019) A Mild and direct site-selective sp2 C–H silylation
of (poly)azines. J Am Chem Soc 141:127–132
83. Kakiuchi F, Igi K, Matsumoto M, Hayamizu T, Chatani N, Murai S (2002) A new chelationassistance mode for a ruthenium-catalyzed silylation at the C–H bond in aromatic ring with
hydrosilanes. Chem Lett 31:396–397
84. Kakiuchi F, Matsumoto M, Tsuchiya K, Igi K, Hayamizu T, Chatani N, Murai S (2003) The
ruthenium-catalyzed silylation of aromatic C–H bonds with triethylsilane. J Organomet Chem
686:134–144
85. Kakiuchi F, Tsuchiya K, Matsumoto M, Mizushima E, Chatani N (2004) Ru3(CO)12Catalyzed silylation of benzylic C−H bonds in arylpyridines and arylpyrazoles with
hydrosilanes via C − H bond cleavage. J Am Chem Soc 126:12792–12793
86. Karmel C, Chen Z, Hartwig JF (2019) Iridium-catalyzed silylation of C–H bonds in unactivated arenes: a sterically encumbered phenanthroline ligand accelerates catalysis. J Am Chem
Soc 141:7063–7072
87. Karmel C, Hartwig JF (2020) Mechanism of the iridium-catalyzed silylation of aromatic C–H
bonds. J Am Chem Soc 142:10494–10505
88. Karmel C, Rubel CZ, Kharitonova EV, Hartwig JF (2020) Iridium-catalyzed silylation of
five-membered heteroarenes: high sterically derived selectivity from a pyridyl-imidazoline
ligand. Angew Chem Int Ed 59:6074–6081
89. Ka´ zmierczak J, Kuci´ nski K, Lewandowski D, Hreczycho G (2019) Ru-Catalyzed dehydrogenative silylation of POSS-silanols with hydrosilanes: its introduction to one-pot synthesis.
Inorg Chem 58:1201–1207
90. Oyamada J, Nishiura M, Hou Z (2011) Scandium-catalyzed silylation of aromatic C–H bonds.
Angew Chem Int Ed 50:10720–10723
91. Richter SC, Oestreich M (2020) Emerging strategies for C–H silylation. Trends Chem 2:13–27
92. Saiki T, Nishio Y, Ishiyama T, Miyaura N (2006) Improvements of efficiency and regioselectivity in the iridium(i)-catalyzed aromatic CH silylation of arenes with fluorodisilanes.
Organometallics 25:6068–6073