ACS Catalysis
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Catalyzed Alkyl–Alkyl Kumada Coupling Reactions. J. Am. Chem. Soc. 2013, 135, 12004-
12012; (e) Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Catalytic Asymmetric Reductive
Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones. J. Am.
Chem. Soc. 2013, 135, 7442-7445; (f) León, T.; Correa, A.; Martin, R. Ni-Catalyzed Direct
Carboxylation of Benzyl Halides with CO2. J. Am. Chem. Soc. 2013, 135, 1221-1224; (g)
Biswas, S.; Weix, D. J. Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile
Coupling of Aryl Halides with Alkyl Halides. J. Am. Chem. Soc. 2013, 135, 16192-16197; (h)
Breitenfeld, J.; Wodrich, M. D.; Hu, X. Bimetallic Oxidative Addition in Nickel-Catalyzed
Alkyl–Aryl Kumada Coupling Reactions. Organometallics 2014, 33, 5708-5715; (i) Schley, N.
D.; Fu, G. C. Nickel-Catalyzed Negishi Arylations of Propargylic Bromides: A Mechanistic
Investigation. J. Am. Chem. Soc. 2014, 136, 16588-16593; (j) Sayyed, F. B.; Sakaki, S. The
Crucial Roles of MgCl2 as a Non-Innocent Additive in the Ni-Catalyzed Carboxylation of
Benzyl Halide with CO2. Chem. Commun. 2014, 50, 13026-13029; (k) Börjesson, M.; Moragas,
T.; Martin, R. Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO2. J. Am.
Chem. Soc. 2016, 138, 7504-7507.
11. For examples where Ni(I) complexes are proposed in cross-coupling and related reactions
with sp3 hybridized substrates see references 4-6 and: (a) Gao, C.-Y.; Cao, X.; Yang, L.-M.
Nickel-Catalyzed Cross-Coupling of Diarylamines with Haloarenes. Org. Biomol. Chem. 2009,
7, 3922-3925; (b) Velian, A.; Lin, S.; Miller, A. J. M.; Day, M. W.; Agapie, T. Synthesis and
C−C Coupling Reactivity of a Dinuclear Ni(I)−Ni(I) Complex Supported by a Terphenyl
Diphosphine. J. Am. Chem. Soc. 2010, 132, 6296-6297; (c) Miyazaki, S.; Koga, Y.; Matsumoto,
T.; Matsubara, K. A New Aspect of Nickel-Catalyzed Grignard Cross-Coupling Reactions:
Selective Synthesis, Structure, and Catalytic Behavior of a T-Shape Three-Coordinate Nickel(I)
Chloride Bearing a Bulky NHC Ligand. Chem. Commun. 2010, 46, 1932-1934; (d) Zhang, K.;
Conda-Sheridan, M.; R. Cooke, S.; Louie, J. N-Heterocyclic Carbene Bound Nickel(I)
Complexes and Their Roles in Catalysis. Organometallics 2011, 30, 2546-2552; (e) Nagao, S.;
Matsumoto, T.; Koga, Y.; Matsubara, K. Monovalent Nickel Complex Bearing a Bulky N-
Heterocyclic Carbene Catalyzes Buchwald–Hartwig Amination of Aryl Halides under Mild
Conditions. Chem. Lett. 2011, 40, 1036-1038; (f) Fujihara, T.; Nogi, K.; Xu, T.; Terao, J.; Tsuji,
Y. Nickel-Catalyzed Carboxylation of Aryl and Vinyl Chlorides Employing Carbon Dioxide. J.
Am. Chem. Soc. 2012, 134, 9106-9109; (g) Sayyed, F. B.; Tsuji, Y.; Sakaki, S. The Crucial Role
of a Ni(I) Intermediate in Ni-Catalyzed Carboxylation of Aryl Chloride with CO2: A Theoretical
Study. Chem. Commun. 2013, 49, 10715-10717; (h) Cornella, J.; Gómez-Bengoa, E.; Martin, R.
Combined Experimental and Theoretical Study on the Reductive Cleavage of Inert C–O Bonds
with Silanes: Ruling out a Classical Ni(0)/Ni(II) Catalytic Couple and Evidence for Ni(I)
Intermediates. J. Am. Chem. Soc. 2013, 135, 1997-2009; (i) Page, M. J.; Lu, W. Y.; Poulten, R.
C.; Carter, E.; Algarra, A. G.; Kariuki, B. M.; Macgregor, S. A.; Mahon, M. F.; Cavell, K. J.;
Murphy, D. M.; Whittlesey, M. K. Three-Coordinate Nickel(I) Complexes Stabilised by Six-,
Seven- and Eight-Membered Ring N-Heterocyclic Carbenes: Synthesis, EPR/DFT Studies and
Catalytic Activity. Chem. Eur. J. 2013, 19, 2158-2167; (j) Correa, A.; León, T.; Martin, R. Ni-
Catalyzed Carboxylation of C(sp2)– and C(sp3)–O Bonds with CO2. J. Am. Chem. Soc. 2014,
136, 1062-1069; (k) Wu, J.; Nova, A.; Balcells, D.; Brudvig, G. W.; Dai, W.; Guard, L. M.;
Hazari, N.; Lin, P.-H.; Pokhrel, R.; Takase, M. K. Nickel(I) Monomers and Dimers with
Cyclopentadienyl and Indenyl Ligands. Chem. Eur. J. 2014, 20, 5327-5337; (l) Guard, L. M.;
Mohadjer Beromi, M.; Brudvig, G. W.; Hazari, N.; Vinyard, D. J. Comparison of dppf-
Supported Ni Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of
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