Journal of the American Chemical Society
Page 8 of 10
3.
in Total Synthesis. Chem. Soc. Rev. 2011, 40, 1976-1991.
4. Pouliot, J.-R.; Grenier, F.; Blaskovits, J. T.; Beaupré, S.;
Leclerc, M., Direct (Hetero)arylation Polymerization: Simplicity for
Conjugated Polymer Synthesis. Chem. Rev. 2016, 116, 14225-
14274.
Gutekunst, W. R.; Baran, P. S., C–H Functionalization Logic
2018, 57, 14179-14183; (k) Mei, R.; Sauermann, N.; Oliveira, J. C.
A.; Ackermann, L., Electroremovable Traceless Hydrazides for
Cobalt-Catalyzed Electro-Oxidative C–H/N–H Activation with
Internal Alkynes. J. Am. Chem. Soc. 2018, 140, 7913-7921; (l) Gao,
X.; Wang, P.; Zeng, L.; Tang, S.; Lei, A., Cobalt(II)-Catalyzed
Electrooxidative C–H Amination of Arenes with Alkylamines. J.
Am. Chem. Soc. 2018, 140, 4195-4199; (m) Konishi, M.; Tsuchida,
K.; Sano, K.; Kochi, T.; Kakiuchi, F., Palladium-Catalyzed ortho-
Selective C–H Chlorination of Benzamide Derivatives under Anodic
Oxidation Conditions. J. Org. Chem. 2017, 82, 8716-8724; (n) Yang,
Q.-L.; Li, Y.-Q.; Ma, C.; Fang, P.; Zhang, X.-J.; Mei, T.-S.,
Palladium-Catalyzed C(sp3)–H Oxygenation via Electrochemical
Oxidation. J. Am. Chem. Soc. 2017, 139, 3293-3298; (o) Sauermann,
N.; Meyer, T. H.; Tian, C.; Ackermann, L., Electrochemical Cobalt-
Catalyzed C–H Oxygenation at Room Temperature. J. Am. Chem.
Soc. 2017, 139, 18452-18455; (p) Ma, C.; Zhao, C.-Q.; Li, Y.-Q.;
Zhang, L.-P.; Xu, X.-T.; Zhang, K.; Mei, T.-S., Palladium-Catalyzed
1
2
3
4
5
6
7
8
5.
Selected reviews: (a) Song, G.; Wang, F.; Li, X., C–C, C–O
and C–N Bond Formation via Rhodium(III)-Catalyzed Oxidative C–
H Activation. Chem. Soc. Rev. 2012, 41, 3651-3678; (b) Satoh, T.;
Miura, M., Oxidative Coupling of Aromatic Substrates with Alkynes
and Alkenes under Rhodium Catalysis. Chem. Eur. J. 2010, 16,
11212-11222.
9
6.
(a) Wang, H.; Gao, X.; Lv, Z.; Abdelilah, T.; Lei, A., Recent
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
Advances in Oxidative R1–H/R2–H Cross-Coupling with Hydrogen
Evolution via Photo-/Electrochemistry. Chem. Rev. 2019, 119, 6769-
6787; (b) Waldvogel, S. R.; Lips, S.; Selt, M.; Riehl, B.; Kampf, C.
J., Electrochemical Arylation Reaction. Chem. Rev. 2018, 118, 6706-
6765; (c) Tang, S.; Liu, Y.; Lei, A., Electrochemical Oxidative
Cross-coupling with Hydrogen Evolution: A Green and Sustainable
Way for Bond Formation. Chem 2018, 4, 27-45; (d) Nutting, J. E.;
Rafiee, M.; Stahl, S. S., Tetramethylpiperidine N-Oxyl (TEMPO),
Phthalimide N-Oxyl (PINO), and Related N-Oxyl Species:
Electrochemical Properties and Their Use in Electrocatalytic
Reactions. Chem. Rev. 2018, 118, 4834-4885; (e) Kärkäs, M. D.,
Electrochemical Strategies for C–H Functionalization and C–N
Bond Formation. Chem. Soc. Rev. 2018, 47, 5786-5865; (f) Yan, M.;
Kawamata, Y.; Baran, P. S., Synthetic Organic Electrochemistry:
Calling All Engineers. Angew. Chem. Int. Ed. 2018, 57, 4149-4155;
(g) Möhle, S.; Zirbes, M.; Rodrigo, E.; Gieshoff, T.; Wiebe, A.;
Waldvogel Siegfried, R., Modern Electrochemical Aspects for the
Synthesis of Value‐Added Organic Products. Angew. Chem. Int. Ed.
2018, 57, 6018-6041; (h) Sauermann, N.; Meyer, T. H.; Ackermann,
L., Electrochemical Cobalt-Catalyzed C–H Activation. Chem. Eur.
J. 2018, 16209-16217; (i) Feng, R.; Smith, J. A.; Moeller, K. D.,
Anodic Cyclization Reactions and the Mechanistic Strategies That
Enable Optimization. Acc. Chem. Res. 2017, 50, 2346-2352; (j)
Francke, R.; Little, R. D., Redox Catalysis in Organic
Electrosynthesis: Basic Principles and Recent Developments. Chem.
Soc. Rev. 2014, 43, 2492-2521.
C–H
Activation/C–C
Cross-Coupling
Reactions
via
Electrochemistry. Chem. Commun. 2017, 53, 12189-12192, and
cited references.
9.
For reviews see: (a) Qiu, Y.; Struwe, J.; Ackermann, L.,
Metallaelectro-Catalyzed C–H Activation by Weak Coordination.
Synlett 2019, 30, 1164-1173; (b) Ma, C.; Fang, P.; Mei, T.-S., Recent
Advances in C–H Functionalization Using Electrochemical
Transition Metal Catalysis. ACS Catal. 2018, 8, 7179-7189; (c)
Sauermann, N.; Meyer, T. H.; Qiu, Y.; Ackermann, L.,
Electrocatalytic C–H Activation. ACS Catal. 2018, 8, 7086-7103; (d)
Kärkäs, M. D., Electrochemical Strategies for C–H Functionalization
and C–N Bond Formation. Chem. Soc. Rev. 2018, 47, 5786-5865; (e)
Jiao, K.-J.; Zhao, C.-Q.; Fang, P.; Mei, T.-S., Palladium Catalyzed
C–H Functionalization with Electrochemical Oxidation.
Tetrahedron Lett. 2017, 58, 797-802.
10.
For representative advancees in flow chemistry see: (a) Beil,
S. B.; Uecker, I.; Franzmann, P.; Müller, T.; Waldvogel, S. R., Mild,
Fast, and Easy To Conduct MoCl5-Mediated Dehydrogenative
Coupling Reactions in Flow. Org. Lett. 2018, 20, 4107-4110; (b)
Plutschack, M. B.; Pieber, B.; Gilmore, K.; Seeberger, P. H., The
Hitchhiker’s Guide to Flow Chemistry. Chem. Rev. 2017, 117,
11796-11893; (c) Folgueiras-Amador, A. A.; Wirth, T., Perspectives
in Flow Electrochemistry. J. Flow Chem. 2017, 7, 94-95; (d) Wang,
H.; Pesciaioli, F.; Oliveira, J. C. A.; Warratz, S.; Ackermann, L.,
Synergistic Manganese(I) C–H Activation Catalysis in Continuous
Flow: Chemoselective Hydroarylation. Angew. Chem. Int. Ed. 2017,
56, 15063-15067; (e) Movsisyan, M.; Delbeke, E. I. P.; Berton, J. K.
E. T.; Battilocchio, C.; Ley, S. V.; Stevens, C. V., Taming Hazardous
Chemistry by Continuous Flow Technology. Chem. Soc. Rev. 2016,
45, 4892-4928; (f) Gemoets, H. P. L.; Su, Y.; Shang, M.; Hessel, V.;
Luque, R.; Noël, T., Liquid Phase Oxidation Chemistry in
Continuous-Flow Microreactors. Chem. Soc. Rev. 2016, 45, 83-117;
(g) Tucker, J. W.; Zhang, Y.; Jamison, T. F.; Stephenson, C. R. J.,
Visible-Light Photoredox Catalysis in Flow. Angew. Chem. Int. Ed.
2012, 51, 4144-4147; (h) Noël, T.; Buchwald, S. L., Cross-Coupling
in Flow. Chem. Soc. Rev. 2011, 40, 5010-5029; (i) Santoro, S.;
Ferlin, F.; Ackermann, L.; Vaccaro, L., C–H Functionalization
Reactions Under Flow Conditions. Chem. Soc. Rev. 2019, 48, 2767-
2782.
7.
Meyer, T. H.; Finger, L. H.; Gandeepan, P.; Ackermann, L.,
Resource Economy by Metallaelectrocatalysis: Merging
Electrochemistry and C–H Activation. Trends Chem. 2019, 1, 63-76.
8.
Selected examples: (a) Yang, Q.-L.; Wang, X.-Y.; Wang, T.-
L.; Yang, X.; Liu, D.; Tong, X.; Wu, X.-Y.; Mei, T.-S., Palladium-
Catalyzed Electrochemical C–H Bromination Using NH4Br as the
Brominating Reagent. Org. Lett. 2019, 21, 2645-2649; (b) Zhang, S.-
K.; Samanta, R. C.; Sauermann, N.; Ackermann, L., Nickel-
Catalyzed Electrooxidative C–H Amination: Support for Nickel(IV).
Chem. Eur. J. 2018, 24, 19166-19170; (c) Yang, Q.-L.; Wang, X.-
Y.; Lu, J.-Y.; Zhang, L.-P.; Fang, P.; Mei, T.-S., Copper-Catalyzed
Electrochemical C–H Amination of Arenes with Secondary Amines.
J. Am. Chem. Soc. 2018, 140, 11487-11494; (d) Xu, F.; Li, Y.-J.;
Huang, C.; Xu, H.-C., Ruthenium-Catalyzed Electrochemical
Dehydrogenative Alkyne Annulation. ACS Catal. 2018, 8, 3820-
3824; (e) 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; (f) Tang, S.; Wang, D.; Liu, Y.; Zeng, L.; Lei, A.,
Cobalt-Catalyzed Electrooxidative C–H/N–H [4+2] Annulation with
Ethylene or Ethyne. Nat. Commun. 2018, 9, 798; (g) Shrestha, A.;
Lee, M.; Dunn, A. L.; Sanford, M. S., Palladium-Catalyzed C–H
Bond Acetoxylation via Electrochemical Oxidation. Org. Lett. 2018,
20, 204-207; (h) 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; (i) Qiu, Y.;
Tian, C.; Massignan, L.; Rogge, T.; Ackermann, L., Electrooxidative
Ruthenium-Catalyzed C–H/O–H Annulation by Weak O-
Coordination. Angew. Chem. Int. Ed. 2018, 57, 5818-5822; (j) Qiu,
Y.; Stangier, M.; Meyer, T. H.; Oliveira, J. C. A.; Ackermann, L.,
11.
(a) Pletcher, D.; Green, R. A.; Brown, R. C. D., Flow
Electrolysis Cells for the Synthetic Organic Chemistry Laboratory.
Chem. Rev. 2018, 118, 4573-4591; (b) Atobe, M.; Tateno, H.;
Matsumura, Y., Applications of Flow Microreactors in
Electrosynthetic Processes. Chem. Rev. 2018, 118, 4541-4572.
12.
(a) Peters, B. K.; Rodriguez, K. X.; Reisberg, S. H.; Beil, S.
B.; Hickey, D. P.; Kawamata, Y.; Collins, M.; Starr, J.; Chen, L.;
Udyavara, S.; Klunder, K.; Gorey, T. J.; Anderson, S. L.; Neurock,
M.; Minteer, S. D.; Baran, P. S., Scalable and safe synthetic organic
electroreduction inspired by Li-ion battery chemistry. Science 2019,
363, 838; (b) Laudadio, G.; Barmpoutsis, E.; Schotten, C.; Struik, L.;
Govaerts, S.; Browne, D. L.; Noël, T., Sulfonamide Synthesis
through Electrochemical Oxidative Coupling of Amines and Thiols.
J. Am. Chem. Soc. 2019, 141, 5664-5668; (c) Elsherbini, M.;
Winterson, B.; Alharbi, H.; Folgueiras-Amador, A. A.; Génot, C.;
Iridium-Catalyzed
Electrooxidative
C–H
Activation
by
Chemoselective Redox-Catalyst Cooperation. Angew. Chem. Int. Ed.
ACS Paragon Plus Environment