95
71. Demir AS, Reis O, Emrullahoglu M (2003) Generation of aryl radicals from arylboronic acids
by manganese(III) acetate: synthesis of biaryls and heterobiaryls. J Org Chem 68(2):578–580
72. Ban I, Sudo T, Taniguchi T, Itami K (2008) Copper-mediated C-H bond arylation of arenes
with arylboronic acids. Org Lett 10(16):3607–3609
73. Wen J, Zhang J, Chen S-Y, Li J, Yu X-Q (2008) Iron-mediated direct arylation of unactivated
arenes. Angew Chem Int Ed 47(46):8897–8900
74. Wen J, Qin S, Ma L-F, Dong L, Zhang J, Liu S-S, Duan Y-S, Chen S-Y, Hu C-W, Yu X-Q
(2010) Iron-mediated direct Suzuki-Miyaura reaction: a new method for the ortho-arylation
of pyrrole and pyridine. Org Lett 12(12):2694–2697
75. Uchiyama N, Shirakawa E, Nishikawa R, Hayashi T (2011) Iron-catalyzed oxidative coupling of arylboronic acids with benzene derivatives through homolytic aromatic substitution.
Chem Commun 47(42):11671–11673
76. Hachiya H, Hirano K, Satoh T, Miura M (2010) Oxidative nickel-air catalysis in C-arylation:
direct cross-coupling of azoles with arylboronic acids using air as sole oxidant. ChemCatChem
2(11):1403–1406
77. Liu D, Liu C, Lei A (2014) Nickel-catalyzed oxidative cross-coupling of arylboronic acids
with olefins. Pure and App Chem 86(3):321–328
78. Yang S, Li B, Wan X, Shi Z (2007) Ortho arylation of acetanilides via Pd(II)-catalyzed C-H
functionalization. J Am Chem Soc 129(19):6066–6067
79. Zhou H, Xu Y-H, Chung W-J, Loh T-P (2009) Palladium-catalyzed direct arylation of cyclic
enamides with aryl silanes by sp2 C-H activation. Angew Chem Int Ed 48(29):5355–5357
80. 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(12):2202–2205
81. Liang Z, Yao B, Zhang Y (2010) Pd(OAc)2-catalyzed regioselective arylation of indoles with
arylsiloxane in acidic medium. Org Lett 12(14):3185–3187
82. Funaki K, Sato T, Oi S (2012) Pd-catalyzed β-selective direct C-H bond arylation of thiophenes with aryltrimethylsilanes. Org Lett 14(24):6186–6189
83. Chu L, Qing F-L (2012) Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes. J Am Chem Soc 134(2):1298–1304
84. Shang M, Sun S-Z, Wang H-L, Laforteza BN, Dai H-X, Yu J-Q (2014) Exceedingly fast
copper(II)-promoted ortho C-H trifluoromethylation of arenes using TMSCF3. Angew Chem
Int Ed 53(39):10439–10442
85. Nakamura E, Yoshikai N (2010) Low-valent iron-catalyzed C-C bond formation-addition,
substitution, and C-H bond activation. J Org Chem 75(18):6061–6067
86. Norinder J, Matsumoto A, Yoshikai N, Nakamura E (2008) Iron-catalyzed direct arylation
through directed C-H bond activation. J Am Chem Soc 130(18):5858–5859
87. Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2009) Iron-catalyzed chemoselective ortho arylation of aryl imines by directed C-H bond activation. Angew Chem Int Ed
48(16):2925–2928
88. Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2010) Iron-catalyzed direct arylation of
aryl pyridines and imines using oxygen as an oxidant. Synlett 2:313–316
89. Shang R, Ilies L, Nakamura E (2017) Iron-catalyzed C-H bond activation. Chem Rev
117(13):9086–9139
90. Ilies L, Okabe J, Yoshikai N, Nakamura E (2010) Iron-catalyzed, directed oxidative arylation
of olefins with organozinc and Grignard reagents. Org Lett 12(12):2838–2840
91. Ilies L, Asako S, Nakamura E (2011) Iron-catalyzed stereospecific activation of olefinic
C-H bonds with Grignard reagent for synthesis of substituted olefins. J Am Chem Soc
133(20):7672–7675
92. Li B, Wu Z-H, Gu Y-F, Sun C-L, Wang B-Q, Shi Z-J (2011) Direct cross-coupling of C-H
bonds with Grignard reagents through cobalt catalysis. Angew Chem Int Ed 50(5):1109–1113
93. Do H-Q, Daugulis O (2010) Copper-catalyzed cyanation of heterocycle carbon-hydrogen
bonds. Org Lett 12(11):2517–2519
3 Oxidative Coupling Reactions Between Hydrocarbons and Organometallic Reagents…
71. Demir AS, Reis O, Emrullahoglu M (2003) Generation of aryl radicals from arylboronic acids
by manganese(III) acetate: synthesis of biaryls and heterobiaryls. J Org Chem 68(2):578–580
72. Ban I, Sudo T, Taniguchi T, Itami K (2008) Copper-mediated C-H bond arylation of arenes
with arylboronic acids. Org Lett 10(16):3607–3609
73. Wen J, Zhang J, Chen S-Y, Li J, Yu X-Q (2008) Iron-mediated direct arylation of unactivated
arenes. Angew Chem Int Ed 47(46):8897–8900
74. Wen J, Qin S, Ma L-F, Dong L, Zhang J, Liu S-S, Duan Y-S, Chen S-Y, Hu C-W, Yu X-Q
(2010) Iron-mediated direct Suzuki-Miyaura reaction: a new method for the ortho-arylation
of pyrrole and pyridine. Org Lett 12(12):2694–2697
75. Uchiyama N, Shirakawa E, Nishikawa R, Hayashi T (2011) Iron-catalyzed oxidative coupling of arylboronic acids with benzene derivatives through homolytic aromatic substitution.
Chem Commun 47(42):11671–11673
76. Hachiya H, Hirano K, Satoh T, Miura M (2010) Oxidative nickel-air catalysis in C-arylation:
direct cross-coupling of azoles with arylboronic acids using air as sole oxidant. ChemCatChem
2(11):1403–1406
77. Liu D, Liu C, Lei A (2014) Nickel-catalyzed oxidative cross-coupling of arylboronic acids
with olefins. Pure and App Chem 86(3):321–328
78. Yang S, Li B, Wan X, Shi Z (2007) Ortho arylation of acetanilides via Pd(II)-catalyzed C-H
functionalization. J Am Chem Soc 129(19):6066–6067
79. Zhou H, Xu Y-H, Chung W-J, Loh T-P (2009) Palladium-catalyzed direct arylation of cyclic
enamides with aryl silanes by sp2 C-H activation. Angew Chem Int Ed 48(29):5355–5357
80. 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(12):2202–2205
81. Liang Z, Yao B, Zhang Y (2010) Pd(OAc)2-catalyzed regioselective arylation of indoles with
arylsiloxane in acidic medium. Org Lett 12(14):3185–3187
82. Funaki K, Sato T, Oi S (2012) Pd-catalyzed β-selective direct C-H bond arylation of thiophenes with aryltrimethylsilanes. Org Lett 14(24):6186–6189
83. Chu L, Qing F-L (2012) Copper-catalyzed direct C-H oxidative trifluoromethylation of heteroarenes. J Am Chem Soc 134(2):1298–1304
84. Shang M, Sun S-Z, Wang H-L, Laforteza BN, Dai H-X, Yu J-Q (2014) Exceedingly fast
copper(II)-promoted ortho C-H trifluoromethylation of arenes using TMSCF3. Angew Chem
Int Ed 53(39):10439–10442
85. Nakamura E, Yoshikai N (2010) Low-valent iron-catalyzed C-C bond formation-addition,
substitution, and C-H bond activation. J Org Chem 75(18):6061–6067
86. Norinder J, Matsumoto A, Yoshikai N, Nakamura E (2008) Iron-catalyzed direct arylation
through directed C-H bond activation. J Am Chem Soc 130(18):5858–5859
87. Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2009) Iron-catalyzed chemoselective ortho arylation of aryl imines by directed C-H bond activation. Angew Chem Int Ed
48(16):2925–2928
88. Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2010) Iron-catalyzed direct arylation of
aryl pyridines and imines using oxygen as an oxidant. Synlett 2:313–316
89. Shang R, Ilies L, Nakamura E (2017) Iron-catalyzed C-H bond activation. Chem Rev
117(13):9086–9139
90. Ilies L, Okabe J, Yoshikai N, Nakamura E (2010) Iron-catalyzed, directed oxidative arylation
of olefins with organozinc and Grignard reagents. Org Lett 12(12):2838–2840
91. Ilies L, Asako S, Nakamura E (2011) Iron-catalyzed stereospecific activation of olefinic
C-H bonds with Grignard reagent for synthesis of substituted olefins. J Am Chem Soc
133(20):7672–7675
92. Li B, Wu Z-H, Gu Y-F, Sun C-L, Wang B-Q, Shi Z-J (2011) Direct cross-coupling of C-H
bonds with Grignard reagents through cobalt catalysis. Angew Chem Int Ed 50(5):1109–1113
93. Do H-Q, Daugulis O (2010) Copper-catalyzed cyanation of heterocycle carbon-hydrogen
bonds. Org Lett 12(11):2517–2519
3 Oxidative Coupling Reactions Between Hydrocarbons and Organometallic Reagents…