Page 9 of 11
ACS Catalysis
Grignard Reagents under Nickel/Magnesium Bimetallic
Cooperation. J. Am. Chem. Soc. 2005, 127, 17978-17979.
11. Yoshikai, N.; Matsuda, H.; Nakamura, E.,
Hydroxyphosphine Ligand for Nickel-Catalyzed Cross-Coupling
through Nickel/Magnesium Bimetallic Cooperation. J. Am. Chem.
Soc. 2009, 131, 9590-9599.
29.
Song, W.; Ackermann, L., Nickel-catalyzed alkyne
1
2
3
4
5
6
7
8
annulation by anilines: versatile indole synthesis by C–H/N–H
functionalization. Chem. Commun. 2013, 49, 6638-6640.
30.
Fagnou, K., Indole Synthesis via Rhodium Catalyzed Oxidative
Coupling of Acetanilides and Internal Alkynes. J. Am. Chem. Soc.
2008, 130, 16474-16475.
Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.;
12.
Wang, J.-R.; Manabe, K., High Ortho Preference in Ni-
Catalyzed Cross-Coupling of Halophenols with Alkyl Grignard
Reagents. Org. Lett. 2009, 11, 741-744.
31.
Ackermann, L., Carboxylate-Assisted Ruthenium-
Catalyzed Alkyne Annulations by C–H/Het–H Bond
Functionalizations. Acc. Chem. Res. 2014, 47, 281-295.
13.
Ackermann, L.; Wechsler, C.; Kapdi, A. R.; Althammer, A.,
9
Air-Stable Diaminophosphine Sulfides as Preligands for Nickel-
Catalyzed Cross-Couplings of Unactivated Fluoro(hetero)arenes.
Synlett 2010, 2010, 294-298.
32.
Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N.,
Indoles from Simple Anilines and Alkynes: Palladium-Catalyzed C-H
Activation Using Dioxygen as the Oxidant. Angew. Chem. Int. Ed.
2009, 48, 4572-4576.
33.
of Internal Alkynes. Synthesis 2014, 46, 1555-1572.
34. Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M., Synthesis of
Highly Substituted Acenes through Rhodium-Catalyzed Oxidative
Coupling of Arylboron Reagents with Alkynes. J. Org. Chem. 2011,
76, 2867-2874.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
14.
Nakamura, Y.; Yoshikai, N.; Ilies, L.; Nakamura, E., Nickel-
Catalyzed Monosubstitution of Polyfluoroarenes with Organozinc
Reagents Using Alkoxydiphosphine Ligand. Org. Lett. 2012, 14,
3316-3319.
Le Bras, J.; Muzart, J., Dehydrogenative Heck Annelations
15.
Guo, W.-J.; Wang, Z.-X., Cross-Coupling of ArX with
ArMgBr Catalyzed by N-Heterocyclic Carbene-Based Nickel
Complexes. J. Org. Chem. 2013, 78, 1054-1061.
16.
O'Neill, M. J.; Riesebeck, T.; Cornella, J., Thorpe–Ingold
35.
Pham, M. V.; Cramer, N., Aromatic Homologation by Non-
Effect in Branch-Selective Alkylation of Unactivated Aryl Fluorides.
Angew. Chem. Int. Ed. 2018, 57, 9103-9107.
Chelate-Assisted RhIII-Catalyzed C-H Functionalization of Arenes
with Alkynes. Angew. Chem. Int. Ed. 2014, 53, 3484-3487.
36.
Gómez Arrayás, R.; Carretero, J. C., RhI/RhIII catalyst-controlled
divergent aryl/heteroaryl C–H bond functionalization of
picolinamides with alkynes. Chem. Sci. 2015, 6, 5802-5814.
17.
Schaub, T.; Backes, M.; Radius, U., Catalytic C−C Bond
Martínez, Á. M.; Echavarren, J.; Alonso, I.; Rodríguez, N.;
Formation Accomplished by Selective C−F Activation of
Perfluorinated Arenes. J. Am. Chem. Soc. 2006, 128, 15964-15965.
18.
Sun, A. D.; Love, J. A., Nickel-Catalyzed Selective
Defluorination to Generate Partially Fluorinated Biaryls. Org. Lett.
2011, 13, 2750-2753.
37.
MisalꢀCastro, L. C.; Obata, A.; Aihara, Y.; Chatani, N.,
Chelation-Assisted Nickel-Catalyzed Oxidative Annulation via
Double C−H Activation/Alkyne Insertion Reaction. Chem. Eur. J.
2016, 22, 1362-1367.
19.
Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N., Nickel-
Catalyzed Suzuki–Miyaura Reaction of Aryl Fluorides. J. Am. Chem.
Soc. 2011, 133, 19505-19511.
38.
He, Z.; Huang, Y., Diverting C–H Annulation Pathways:
20.
Zhou, J.; Berthel, J. H. J.; Kuntze-Fechner, M. W.; Friedrich,
Nickel-Catalyzed Dehydrogenative Homologation of Aromatic
Amides. ACS Catal. 2016, 6, 7814-7823.
39.
Ackermann, L., 3d Transition Metals for C–H Activation. Chem. Rev.
2018.
40.
Activation and Competition between C–H and C–F Bond Activation
at Fluorocarbons. Chem. Rev. 2017, 117, 8710-8753.
A.; Marder, T. B.; Radius, U., NHC Nickel-Catalyzed Suzuki–Miyaura
Cross-Coupling Reactions of Aryl Boronate Esters with
Perfluorobenzenes. J. Org. Chem. 2016, 81, 5789-5794.
Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.;
21.
Ho, Y. A.; Leiendecker, M.; Liu, X.; Wang, C.; Alandini, N.;
Rueping, M., Nickel-Catalyzed Csp2–Csp3 Bond Formation via C–F
Bond Activation. Org. Lett. 2018, 20, 5644-5647.
Eisenstein, O.; Milani, J.; Perutz, R. N., Selectivity of C–H
22.
Yu, D.; Shen, Q.; Lu, L., Selective Palladium-Catalyzed C–F
Activation/Carbon–Carbon Bond Formation of Polyfluoroaryl
Oxazolines. J. Org. Chem. 2012, 77, 1798-1804.
41.
Ghorai, D.; Finger, L. H.; Zanoni, G.; Ackermann, L.,
Bimetallic Nickel Complexes for Aniline C–H Alkylations. ACS Catal.
2018, 8, 11657-11662.
42.
Aminoquinoline-Directed C(sp2)-H Bond Alkenylation by Alkynes.
Angew. Chem. Int. Ed. 2014, 53, 10209-10212.
23.
Yu, D.; Wang, C.-S.; Yao, C.; Shen, Q.; Lu, L., Nickel-
Catalyzed α-Arylation of Zinc Enolates with Polyfluoroarenes via C–
F Bond Activation under Neutral Conditions. Org. Lett. 2014, 16,
5544-5547.
Grigorjeva, L.; Daugulis, O., Cobalt-Catalyzed,
24.
Guimond, N.; Gouliaras, C.; Fagnou, K., Rhodium(III)-
43.
Bennett, M. A.; Wenger, E., The Reactivity of Complexes of
Catalyzed Isoquinolone Synthesis: The N−O Bond as a Handle for
C−N Bond Formation and Catalyst Turnover. J. Am. Chem. Soc.
2010, 132, 6908-6909.
Nickel(0) and Platinum(0) Containing Benzyne and Related Small-
Ring Alkynes. Chem. Ber. 1997, 130, 1029-1042.
44.
of Olefins on Transition-Metal-Catalyzed Cross-Coupling Reactions.
Angew. Chem. Int. Ed. 2008, 47, 840-871.
45.
Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed
Cross-Coupling. J. Am. Chem. Soc. 2015, 137, 5638-5641.
46.
nickel complexes. I. Stability and activation of the alkyl-nickel bonds
of dialkyl (dipyridyl) nickel by coordination with various substituted
olefins. J. Am. Chem. Soc. 1971, 93, 3350-3359.
Johnson, J. B.; Rovis, T., More than Bystanders: The Effect
25.
Ackermann, L.; Lygin, A. V.; Hofmann, N., Ruthenium-
Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds.
Angew. Chem. Int. Ed. 2011, 50, 6379-6382.
Huang, C.-Y.; Doyle, A. G., Electron-Deficient Olefin
26.
Shiota, H.; Ano, Y.; Aihara, Y.; Fukumoto, Y.; Chatani, N.,
Nickel-Catalyzed Chelation-Assisted Transformations Involving
Ortho C–H Bond Activation: Regioselective Oxidative Cycloaddition
of Aromatic Amides to Alkynes. J. Am. Chem. Soc. 2011, 133, 14952-
14955.
Yamamoto, T.; Yamamoto, A.; Ikeda, S., Organo (dipyridyl)
27.
Cera, G.; Haven, T.; Ackermann, L., Iron-catalyzed C–H/N–
H activation by triazole guidance: versatile alkyne annulation. Chem.
Commun. 2017, 53, 6460-6463.
47.
Meyer, T. H.; Oliveira, J. C. A.; Sau, S. C.; Ang, N. W. J.;
Ackermann, L., Electrooxidative Allene Annulations by Mild Cobalt-
Catalyzed C–H Activation. ACS Catal. 2018, 8, 9140-9147.
48.
28.
Tian, C.; Massignan, L.; Meyer, T. H.; Ackermann, L.,
Electrochemical C−H/N−H Activation by Water-Tolerant Cobalt
Catalysis at Room Temperature. Angew. Chem. Int. Ed. 2018, 57,
2383-2387.
Denninger, U.; Schneider, J. J.; Wilke, G.; Goddard, R.;
Krömer, R.; Krüger, C., Transition metal complexes: VIII. An unusual
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