Organometallics
Article
Azobenzenes. ACS Catal. 2018, 8 (2), 1546−1579. (n) Banerjee, S.;
De, P. B.; Pradhan, S.; Shah, T. A.; Punniyamurthy, T. RuII-Catalysed
Regioselective C-N Bond Formation of Indolines and Carbazole with
Acyl Azides. Eur. J. Org. Chem. 2019, 7, 1677−1684. (o) Ma, W.;
Weng, Z.; Fang, X.; Gu, L.; Song, Y.; Ackermann, L. Ruthenium-
Catalyzed C-H Selenylations of Benzamides. Eur. J. Org. Chem. 2019,
1, 41−45.
(5) Chaitanya, M.; Anbarasan, P. Lewis Acid/Brønsted Acid
Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of
C(sp2)-H Bonds with N-(Arylthio)i(a)mides. Org. Lett. 2018, 20,
3362−3366.
(6) Kao, I.-H.; Wang, C.-Y.; Chang, Y.-C.; Wu, C.-L.; Chiu, Y.-J.;
Hong, F.-E. Palladium-catalyzed phosphination and amination
through C-H bond functionalization on biphenyl: Amido-substituent
as directing group. Tetrahedron 2019, 75, 387−397.
(7) Zhao, R.; Yang, Y.; Wang, X.; Ren, P.; Zhang, Q.; Li, D. An
efficient nickel/silver co-catalyzed remote C-H amination of 8-
aminoquinolines with azodicarboxylates at room temperature. RSC
Adv. 2018, 8, 37064.
in Carrageenan-Induced Lung Inflammation. J. Med. Chem. 2015, 58,
8850−8867.
(15) Yoon, U. C.; Mariano, P. S. The Synthetic Potential of
Phthalimide SET Photochemistry. Acc. Chem. Res. 2001, 34, 523−
533.
(16) Zhang, C.; Niu, Z.; Ding, Y.; Zhang, L.; Zhou, Y.; Guo, X.;
Zhang, X.; Zhao, Y.; Yu, G. Highly Concentrated Phthalimide-Based
Anolytes for Organic Redox Flow Batteries with Enhanced
Reversibility. Chem. 2018, 4 (12), 2814−2825.
(17) Shrestha, R.; Mukherjee, P.; Tan, Y.; Litman, Z. C.; Hartwig, J.
F. Sterically Controlled, Palladium-Catalyzed Intermolecular Amina-
tion of Arenes. J. Am. Chem. Soc. 2013, 135, 8480−8483.
(18) Kim, H. J.; Kim, J.; Cho, S. H.; Chang, S. Intermolecular
Oxidative C-N Bond Formation under Metal-Free Conditions:
Control of Chemoselectivity between Aryl sp2 and Benzylic sp3 C-
H Bond Imidation. J. Am. Chem. Soc. 2011, 133 (41), 16382−16385.
(19) Kantak, A. A.; Potavathri, S.; Barham, R. A.; Romano, K. M.;
DeBoef, B. Tandem C-H and N-H Bond Functionalization. J. Am.
Chem. Soc. 2011, 133 (49), 19960−19965.
(20) Marchetti, L.; Kantak, A.; Davis, R.; DeBoef, B. Regioselective
Gold-Catalyzed Oxidative C-N Bond Formation. Org. Lett. 2015, 17,
358−361.
(8) Tran, L. D.; Roane, J.; Daugulis, O. Directed Amination of Non-
Acidic Arene C-H Bonds by a Copper-Silver Catalytic System. Angew.
Chem., Int. Ed. 2013, 52, 6043−6046.
(21) Yu, S.; Wan, B.; Li, X. Rhodium(III)-Catalyzed C-H Activation
and Amidation of Arenes Using N-Arenesulfonated Imides as
Amidating Reagents. Org. Lett. 2013, 15, 3706−3709.
(9) (a) Corbin, J. R.; Schomaker, J. M. Tunable differentiation of
tertiary C-H bonds in intramolecular transition metal-catalyzed
nitrene transfer reactions. Chem. Commun. 2017, 53, 4346−4349.
(b) Dolan, N. S.; Scamp, R. J.; Yang, T.; Berry, J. F.; Schomaker, J. M.
Catalyst-Controlled and Tunable, Chemoselective Silver-Catalyzed
Intermolecular Nitrene Transfer: Experimental and Computational
Studies. J. Am. Chem. Soc. 2016, 138, 14658−14667. (c) Chen, Z.;
Ren, N.; Ma, X.; Nie, J.; Zhang, F.-G.; Ma, J.-A. Silver-Catalyzed [3 +
3] Dipolar Cycloaddition of Trifluorodiazoethane and Glycine
Imines: Access to Highly Functionalized Trifluoromethyl-Substituted
Triazines and Pyridines. ACS Catal. 2019, 9 (5), 4600−4608.
(d) Alderson, J. M.; Corbin, J. R.; Schomaker, J. M. Tunable, Chemo-
and Site-Selective Nitrene Transfer Reactions through the Rational
Design of Silver(I) Catalysts. Acc. Chem. Res. 2017, 50, 2147−2158.
(e) Huang, M.; Yang, T.; Paretsky, J. D.; Berry, J. F.; Schomaker, J. M.
Inverting Steric Effects: Using “Attractive” Noncovalent Interactions
To Direct Silver-Catalyzed Nitrene Transfer. J. Am. Chem. Soc. 2017,
139, 17376−17386. (f) Alderson, J. M.; Corbin, J. R.; Schomaker, J.
M. Investigation of transition metal-catalyzed nitrene transfer
reactions in water. Bioorg. Med. Chem. 2018, 26, 5270−5273.
(10) Zhu, H.; Sun, S.; Qiao, H.; Yang, F.; Kang, J.; Wu, Y.; Wu, Y.
Silver(I)-Catalyzed C4-H Amination of 1-Naphthylamine Derivatives
with Azodicarboxylates. Org. Lett. 2018, 20 (3), 620−623. (b) Cho, S.
H.; Kim, J.; Lee, S. Y.; Chang, S. Silver-Mediated Direct Amination of
Benzoxazoles: Tuning the Amino Group Source from Formamides to
Parent Amines. Angew. Chem., Int. Ed. 2009, 48, 9127−9130. (c) Kim,
J.; Cho, S. H.; Joseph, J.; Chang, S. Cobalt- and Manganese-Catalyzed
Direct Amination of Azoles under Mild Reaction Conditions and the
Mechanistic Details. Angew. Chem., Int. Ed. 2010, 49, 9899−9903.
(11) Osby, J. O.; Martin, M. G.; Ganem, B. An Exceptionally Mild
Deprotection of Phthalimides. Tetrahedron Lett. 1984, 25, 2093−
2096. (b) Khan, M. N. Kinetic Evidence for the Occurrence of a
Stepwise Mechanism in the Hydrazinolysis of Phthalimide. J. Org.
Chem. 1995, 60, 4536−4541.
(22) Xu, H.; Qiao, X.; Yang, S.; Shen, Z. Cu-Catalyzed Direct
Amidation of Aromatic C-H Bonds: An Access to Arylamines. J. Org.
Chem. 2014, 79 (10), 4414−4422.
(23) Allen, L. J.; Cabrera, P. J.; Lee, M.; Sanford, M. S. N-
Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible
Light Photocatalyzed Room Temperature C-H Amination of Arenes
and Heteroarenes. J. Am. Chem. Soc. 2014, 136 (15), 5607−5610.
(24) Patil, M. R.; Dedhia, N. P.; Kapdi, A. R.; Kumar, A. V.
Cobalt(II)/N-Hydroxyphthalimide-Catalyzed Cross-Dehydrogenative
Coupling Reaction at Room Temperature under Aerobic Condition. J.
Org. Chem. 2018, 83, 4477−4490.
(25) Yadav, M. R.; Shankar, M.; Ramesh, E.; Ghosh, K.; Sahoo, A. K.
Ruthenium-Catalyzed ortho-C-H Mono- and Di-Imidation of Arenes
with N-Tosyloxyphthalimide. Org. Lett. 2015, 17, 1886−1889.
(26) Yu, S.; Wan, B.; Li, X. Rhodium(III)-Catalyzed C-H Activation
and Amidation of Arenes Using N-Arenesulfonated Imides as
Amidating Reagents. Org. Lett. 2013, 15, 3706−3709.
(27) Kim, H.; Kim, T.; Lee, D. G.; Roh, S. W.; Lee, C. Nitrogen-
Centered Radical-Mediated C-H Imidation of Arenes and Hetero-
arenes via Visible Light Induced Photocatalysis. Chem. Commun.
2014, 50, 9273−9276.
(28) Wu, J.; Zhou, Y.; Zhou, Y.; Chiang, Ch.-W.; Lei, A. Electro-
oxidative C(sp3)-H Amination of Azoles via Intermolecular Oxidative
C(sp3)-H/N-H Cross-Coupling. ACS Catal. 2017, 7 (12), 8320−
8323.
(29) Gao, W.-J.; Li, W.-C.; Zeng, C.-C.; Tian, H.-Y.; Hu, L.-M.;
Little, R. D. Electrochemically Initiated Oxidative Amination of
Benzoxazoles Using Tetraalkylammonium Halides As Redox Cata-
lysts. J. Org. Chem. 2014, 79, 9613−9618.
(30) Sauermann, N.; Mei, R.; Ackermann, L. Electrochemical C-H
Amination by Cobalt Catalysis in a Renewable Solvent. Angew. Chem.,
Int. Ed. 2018, 57, 5090−5094.
(12) Casal, J. J.; Bollini, M.; Lombardo, M. E.; Bruno, A. M.
Thalidomide analogues: Tumor necrosis factor-alpha inhibitors and
their evaluation as anti-inflammatory agents. Eur. J. Pharm. Sci. 2016,
83, 114−119.
(13) Capitosti, S. M.; Hansen, T. P.; Brown, M. L. Thalidomide
analogues demonstrate dual inhibition of both angiogenesis and
prostate cancer. Bioorg. Med. Chem. 2004, 12, 327−336.
(14) Bhat, M. A.; Al-Omar, M. A.; Ansari, M. A.; Zoheir, K. M. A.;
Imam, F.; Attia, S. M.; Bakheet, S. A.; Nadeem, A.; Korashy, H. M.;
Voronkov, A.; Berishvili, V.; Ahmad, S. F. Design and Synthesis of N-
Arylphthalimides as Inhibitors of Glucocorticoid-Induced TNF
Receptor-Related Protein, Proinflammatory Mediators, and Cytokines
(31) Qiu, Y.; Struwe, J.; Meyer, T. H.; Oliveira, J. C. A.; Ackermann.
Catalyst- and Reagent-Free Electrochemical Azole C-H Amination. L.
Chem. - Eur. J. 2018, 24, 12784−12789.
(32) Gao, X.; Wang, P.; Zeng, L.; Tang, S.; Lei, A. Cobalt(II)-
Catalyzed Electrooxidative C-H Amination of Arenes with Alkyl-
amines. J. Am. Chem. Soc. 2018, 140, 4195−4199.
(33) Kathiravan, S.; Suriyanarayanan, S.; Nicholls, I. A. Electro-
oxidative Amination of sp2 C-H Bonds: Coupling of Amines with Aryl
Amides via Copper Catalysis. Org. Lett. 2019, 21 (7), 1968−1972.
(34) Dudkina, Y. B.; Fayzullin, R. R.; Lyssenko, K. A.; Gubaidullin,
A. T.; Kholin, K. V.; Levitskaya, A. I.; Balakina, M. Yu.; Budnikova, Y.
H. Cyclometalated Nickel Complexes as Key Intermediates in
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