ACS Catalysis
Page 6 of 7
10. (a) Corcoran, E. B.; Pirnot, M. T.; Lin, S. S.; Dreher, S. D.;
17. Afagh, N. A.; Yudin, A. K., Chemoselectivity and the Curious
Reactivity Preferences of Functional Groups. Angew. Chem. Int.
Ed. 2010, 49, 262-310.
18. Humphrey, G. R.; Kuethe, J. T., Practical methodologies for the
synthesis of indoles. Chem. Rev. 2006, 106, 2875-2911.
19. (a) Smith, W. J.; Sawyer, J. S., A novel and selective method for
the N-arylation of indoles mediated by KF/Al2O3. Tetrahedron Lett.
1996, 37, 299-302; (b) Xu, H.; Fan, L. L., Microwave-assisted N-
arylation of indoles via C(sp(2))-N(sp(2)) bond formation by
aromatic nucleophilic substitution reactions. Z. Naturforsch. B
2008, 63, 298-302; (c) Iqbal, M. A.; Mehmood, H.; Lv, J. Y.; Hua,
R. M., Base-Promoted SNAr Reactions of Fluoro- and
Chloroarenes as a Route to N-Aryl Indoles and Carbazoles.
Molecules 2019, 24, 1145.
DiRocco, D. A.; Davies, I. W.; Buchwald, S. L.; MacMillan, D.
W. C., Aryl amination using ligand-free Ni(II) salts and photoredox
catalysis. Science 2016, 353, 279-283; (b) Oderinde, M. S.; Jones,
N. H.; Juneau, A.; Frenette, M.; Aquila, B.; Tentarelli, S.;
Robbins, D. W.; Johannes, J. W., Highly Chemoselective Iridium
Photoredox and Nickel Catalysis for the Cross-Coupling of Primary
Aryl Amines with Aryl Halides. Angew. Chem. Int. Ed. 2016, 55,
13219-13223; (c) Key, R. J.; Vannucci, A. K., Nickel Dual
Photoredox Catalysis for the Synthesis of Aryl Amines.
Organometallics 2018, 37, 1468-1472; (d) Lim, C. H.; Kudisch,
1
2
3
4
5
6
7
8
M.;
Liu, B.; Miyake, G. M., C-N Cross-Coupling via
9
Photoexcitation of Nickel-Amine Complexes. J. Am. Chem. Soc.
2018, 140, 7667-7673; (e) Liu, Y. Y.; Liang, D.; Lu, L. Q.; Xiao,
W. J., Practical heterogeneous photoredox/nickel dual catalysis for
C-N and C-O coupling reactions. Chem. Commun. 2019, 55, 4853-
4856.
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
20. Pawar, G. G.; Wu, H. B.; De, S.; Ma, D. W., Copper(I) Oxide/N,N-
Bis[(2-furyl)methyl]oxalamide-Catalyzed
Coupling
of
(Hetero)aryl Halides and Nitrogen Heterocycles at Low Catalytic
Loading. Adv. Synth. Catal. 2017, 359, 1631-1636.
11. (a) Li, C.; Kawamata, Y.; Nakamura, H.; Vantourout, J. C.; Liu,
Z. Q.; Hou, Q. L.; Bao, D. H.; Starr, J. T.; Chen, J. S.; Yan, M.;
Baran, P. S., Electrochemically Enabled, Nickel-Catalyzed
Amination. Angew. Chem. Int. Ed. 2017, 56, 13088-13093; (b)
Kawamata, Y.; Vantourout, J. C.; Hickey, D. P.; Bai, P.; Chen,
L.; Hou, Q.; Qiao, W.; Barman, K.; Edwards, M. A.; Garrido-
Castro, A. F.; deGruyter, J. N.; Nakamura, H.; Knouse, K.; Qin,
C.; Clay, K. J.; Bao, D.; Li, C.; Starr, J. T.; Garcia-Irizarry, C.;
Sach, N.; White, H. S.; Neurock, M.; Minteer, S. D.; Baran, P. S.,
Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope,
Mechanism, and Applications. J. Am. Chem. Soc. 2019, 141, 6392-
6402.
12. (a) Stradiotto, M.; Lundgren, R. J., Ligand Design in Metal
Chemistry: Reactivity and Catalysis. John Wiley & Sons, Ltd:
Chichester, West Sussex, UK, 2016; (b) Balcells, D.; Nova, A.,
Designing Pd and Ni Catalysts for Cross-Coupling Reactions by
Minimizing Off-Cycle Species. ACS Catal. 2018, 8, 3499-3515.
13. Pringle, P. G.; Smith, M. B., Phosphatrioxaadamantane ligands. In
Phosphorus(III) Ligands in Homogeneous Catalysis: Design and
Synthesis, Kamer, P. C. J.; van Leeuwen, P. W. N. M., Eds. John
Wiley & Sons Ltd.: Chichester, UK, 2012; pp 391-404.
14. Lavoie, C. M.; McDonald, R.; Johnson, E. R.; Stradiotto, M.,
Bisphosphine-Ligated Nickel Pre-catalysts in C(sp(2))-N Cross-
Couplings of Aryl Chlorides: A Comparison of Nickel(I) and
Nickel(II). Adv. Synth. Catal. 2017, 359, 2972-2980.
15. (a) Bajo, S.; Laidlaw, G.; Kennedy, A. R.; Sproules, S.; Nelson,
D. J., Oxidative Addition of Aryl Electrophiles to a Prototypical
Nickel(0) Complex: Mechanism and Structure/Reactivity
Relationships. Organometallics 2017, 36, 1662-1672; (b) Beromi,
M. M.; Banerjee, G.; Brudvig, G. W.; Charboneau, D. J.; Hazari,
N.; Lant, H. M. C.; Mercado, B. Q., Modifications to the Aryl
Group of dppf-Ligated Ni sigma-Aryl Precatalysts: Impact on
Speciation and Catalytic Activity in Suzuki-Miyaura Coupling
Reactions. Organometallics 2018, 37, 3943-3955.
16. (a) Lavoie, C. M.; MacQueen, P. M.; Rotta-Loria, N. L.;
Sawatzky, R. S.; Borzenko, A.; Chisholm, A. J.; Hargreaves, B.
K. V.; McDonald, R.; Ferguson, M. J.; Stradiotto, M., Challenging
nickel-catalysed amine arylations enabled by tailored ancillary
ligand design. Nat. Commun. 2016, 7, 11073; (b) Lavoie, C. M.;
MacQueen, P. M.; Stradiotto, M., Nickel-Catalyzed N-Arylation of
Primary Amides and Lactams with Activated (Hetero)aryl
Electrophiles. Chem. Eur. J. 2016, 22, 18752-18755; (c) Tassone,
J. P.; MacQueen, P. M.; Lavoie, C. M.; Ferguson, M. J.;
McDonald, R.; Stradiotto, M., Nickel-Catalyzed N-Arylation of
Cyclopropylamine and Related Ammonium Salts with (Hetero)aryl
(Pseudo)halides at Room Temperature. ACS Catal. 2017, 7, 6048-
6059; (d) Tassone, J. P.; England, E. V.; MacQueen, P. M.;
Ferguson, M. J.; Stradiotto, M., PhPAd-DalPhos: Ligand-Enabled,
Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Electrophiles
with Bulky Primary Alkylamines. Angew. Chem. Int. Ed. 2019, 58,
2485-2489; (e) Clark, J. S. K.; Ferguson, M. J.; McDonald, R.;
Stradiotto, M., PAd2-DalPhos Enables the Nickel-Catalyzed C-N
Cross-Coupling of Primary Heteroarylamines and (Hetero)aryl
Chlorides. Angew. Chem. Int. Ed. 2019, 58, 6391-6395.
21. (a) Rull, S. G.; Blandez, J. F.; Fructos, M. R.; Belderrain, T. R.;
Nicasio, M. C., C-N Coupling of Indoles and Carbazoles with
Aromatic Chlorides Catalyzed by a Single-Component NHC-
Nickel(0) Precursor. Adv. Synth. Catal. 2015, 357, 907-911; (b)
Rull, S. G.; Funes-Ardoiz, I.; Maya, C.; Maseras, F.; Fructos, M.
R.; Belderrain, T. R.; Nicasio, M. C., Elucidating the Mechanism
of Aryl Aminations Mediated by NHC-Supported Nickel
Complexes: Evidence for a Nonradical Ni(0)/Ni(II) Pathway. ACS
Catal. 2018, 8, 3733-3742.
22. (a) Old, D. W.; Harris, M. C.; Buchwald, S. L., Efficient
palladium-catalyzed N-arylation of indoles. Org. Lett. 2000, 2,
1403-1406; (b) Crawford, S. M.; Lavery, C. B.; Stradiotto, M.,
BippyPhos: A Single Ligand With Unprecedented Scope in the
Buchwald-Hartwig Amination of (Hetero) aryl Chlorides. Chem.
Eur. J. 2013, 19, 16760-16771.
23. Joucla, L.; Djakovitch, L., Transition Metal-Catalysed, Direct and
Site-Selective N1-, C2-or C3-Arylation of the Indole Nucleus: 20
Years of Improvements. Adv. Synth. Catal. 2009, 351, 673-714.
24. Tydlitát, J.; Fecková, M.; le Poul, P.; Pytela, O.; Klikar, M.;
Rodríguez-López, J.; Robin-le Guen, F.; Achelle, S., Influence of
Donor-Substituents on Triphenylamine Chromophores Bearing
Pyridine Fragments. Eur. J. Org. Chem. 2019, 1921-1930.
25. (a) Gaillard, S.; Elmkaddem, M. K.; Fischmeister, C.; Thomas,
C. M.; Renaud, J.-L., Highly efficient and economic synthesis of
new substituted amino-bispyridyl derivatives via copper and
palladium catalysis. Tetrahedron Lett. 2008, 49, 3471-3474; (b)
Tlili, A.; Monnier, F.; Taillefer, M., Selective one-pot synthesis of
symmetrical and unsymmetrical di- and triarylamines with a
ligandless copper catalytic system. Chem. Commun. 2012, 48,
6408–6410; (c) Swarts, A. J.; Mapolie, S. F., The synthesis and
application of novel Ni(II) N-alkyl dipyridylaldiminato complexes
as selective ethylene oligomerisation catalysts. Dalton Trans. 2014,
43, 9892-900; (d) Marion, R.; Sguerra, F.; Di Meo, F.; Sauvageot,
E.; Lohier, J. F.; Daniellou, R.; Renaud, J. L.; Linares, M.;
Hamel, M.; Gaillard, S., NHC copper(I) complexes bearing
dipyridylamine
ligands:
synthesis,
structural,
and
photoluminescent studies. Inorg. Chem. 2014, 53, 9181-9191.
26. Schranck, J.; Tlili, A., Transition-Metal-Catalyzed Monoarylation
of Ammonia. ACS Catal. 2018, 8, 405-418.
27. Fernandez-Perez, H.; Etayo, P.; Panossian, A.; Vidal-Ferran, A.,
Phosphine-Phosphinite and Phosphine-Phosphite Ligands:
Preparation and Applications in Asymmetric Catalysis. Chem. Rev.
2011, 111, 2119-2176.
28. Hazari, N.; Melvin, P. R.; Beromi, M. M., Well-defined nickel and
palladium precatalysts for cross-coupling. Nat. Rev. Chem. 2017,
1, 0025.
29. (a) Borzenko, A.; Rotta-Loria, N. L.; MacQueen, P. M.; Lavoie,
C. M.;
McDonald, R.; Stradiotto, M., Nickel-Catalyzed
Monoarylation of Ammonia. Angew. Chem. Int. Ed. 2015, 54,
3773-3777; (b) Green, R. A.; Hartwig, J. F., Nickel-Catalyzed
Amination of Aryl Chlorides with Ammonia or Ammonium Salts.
Angew. Chem. Int. Ed. 2015, 54, 3768-3772; (c) Schranck, J.;
Furer, P.; Hartmann, V.; Tlili, A., Nickel‐Catalyzed Amination of
Aryl Carbamates with Ammonia. Eur. J. Org. Chem. 2017, 3496-
3500; (d) MacQueen, P. M., Stradiotto, M., Nickel-Catalyzed
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