1 Fu, N., Sauer, G. S., Saha, A., Loo, A. & Lin, S. Metal-catalyzed electrochemical diazidation of alkenes. Science 357, 575-579, (2017).
2 B. Zhang et al., Ni-Electrocatalytic C(sp3)–C(sp3) Doubly Decarboxylative Coupling. Nature, (2022): 10.1038/s41586-022-04691-4.
3 Xiong, P. & Xu, H.-C. Chemistry with Electrochemically Generated N-Centered Radicals. Acc. Chem. Res. 52, 3339-3350, (2019).
4 Yan, M., Kawamata, Y. & Baran, P. S. Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance. Chem. Rev. 117, 13230-13319, (2017).
5 X. Dong, J. L. Roeckl, S. R. Waldvogel, B. Morandi, Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations. Science 371, 507-514 (2021).
6 T. Shen, T. H. Lambert, Electrophotocatalytic diamination of vicinal C–H bonds. Science 371, 620-626 (2021).
7 Novaes, L. F. T., Liu, J., Shen, Y., Lu, L., Meinhardt, J. M. & Lin, S. Electrocatalysis as an enabling technology for organic synthesis. Chem. Soc. Rev. 50, 7941-8002, (2021).
8 Meyer, T. H., Choi, I., Tian, C. & Ackermann, L. Powering the Future: How Can Electrochemistry Make a Difference in Organic Synthesis? Chem 6, 2484-2496, (2020).
9 Jiao, K.-J., Xing, Y.-K., Yang, Q.-L., Qiu, H. & Mei, T.-S. Site-Selective C–H Functionalization via Synergistic Use of Electrochemistry and Transition Metal Catalysis. Acc. Chem. Res. 53, 300-310, (2020).
10 Ackermann, L. Metalla-electrocatalyzed C–H Activation by Earth-Abundant 3d Metals and Beyond. Acc. Chem. Res. 53, 84-104, (2020).
11 Ma, C., Fang, P. & Mei, T.-S. Recent Advances in C–H Functionalization Using Electrochemical Transition Metal Catalysis. ACS Catal. 8, 7179-7189, (2018).
12 Kakiuchi, F. et al. Palladium-Catalyzed Aromatic C−H Halogenation with Hydrogen Halides by Means of Electrochemical Oxidation. J. Am. Chem. Soc. 131, 11310-11311, (2009).
13 Yang, Q.-L. et al. Palladium-Catalyzed C(sp3)–H Oxygenation via Electrochemical Oxidation. J. Am. Chem. Soc. 139, 3293-3298, (2017).
14 Dhawa, U. et al. Enantioselective Pallada-Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes. Angew. Chem. Int. Ed. 59, 13451-13457, (2020).
15 Amatore, C., Cammoun, C. & Jutand, A. Electrochemical Recycling of Benzoquinone in the Pd/Benzoquinone-Catalyzed Heck-Type Reactions from Arenes. Adv. Synth. Catal. 349, 292-296, (2007).
16 Sambiagio, C. et al. A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry. Chem. Soc. Rev. 47, 6603-6743, (2018).
17 Rogge, T. et al. C–H activation. Nat. Rev. Methods Primers 1, 43, (2021).
18 He, J., Wasa, M., Chan, K. S. L., Shao, Q. & Yu, J.-Q. Palladium-Catalyzed Transformations of Alkyl C–H Bonds. Chem. Rev. 117, 8754-8786, (2017).
19 Zhang, L. & Ritter, T. A Perspective on Late-Stage Aromatic C–H Bond Functionalization. J. Am. Chem. Soc. 144, 2399-2414, (2022).
20 J. Wencel-Delord, F. Glorius, C–H bond activation enables the rapid construction and late-stage diversification of functional molecules. Nat. Chem. 5, 369-375 (2013).
21 Cernak, T., Dykstra, K. D., Tyagarajan, S., Vachal, P. & Krska, S. W. The medicinal chemist's toolbox for late stage functionalization of drug-like molecules. Chem. Soc. Rev. 45, 546-576, (2016).
22 Meng, G. et al. Achieving Site-Selectivity for C–H Activation Processes Based on Distance and Geometry: A Carpenter’s Approach. J. Am. Chem. Soc. 142, 10571, (2020).
23 D. A. Colby, R. G. Bergman, J. A. Ellman, Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond Activation. Chem. Rev. 110, 624–655 (2010).
24 Lewis, J. C., Coelho, P. S. & Arnold, F. H. Enzymatic functionalization of carbon–hydrogen bonds. Chem. Soc. Rev. 40, 2003-2021, (2011).
25 Wedi, P. & van Gemmeren, M. Arene-Limited Nondirected C−H Activation of Arenes. Angew. Chem. Int. Ed. 57, 13016-13027, (2018).
26 Jia, C., Kitamura, T. & Fujiwara, Y. Catalytic Functionalization of Arenes and Alkanes via C−H Bond Activation. Acc. Chem. Res. 34, 633-639, (2001).
27 Wang, P. et al. Ligand-accelerated non-directed C–H functionalization of arenes. Nature 551, 489-493, (2017).
28 Zhang, Y.-H., Shi, B.-F. & Yu, J.-Q. Pd(II)-Catalyzed Olefination of Electron-Deficient Arenes Using 2,6-Dialkylpyridine Ligands. J. Am. Chem. Soc. 131, 5072-5074, (2009).
29 Cook, A. K. & Sanford, M. S. Mechanism of the Palladium-Catalyzed Arene C–H Acetoxylation: A Comparison of Catalysts and Ligand Effects. J. Am. Chem. Soc. 137, 3109-3118, (2015).
30 Cook, A. K., Emmert, M. H. & Sanford, M. S. Steric Control of Site Selectivity in the Pd-Catalyzed C–H Acetoxylation of Simple Arenes. Org. Lett. 15, 5428-5431, (2013).
31 Kubota, A., Emmert, M. H. & Sanford, M. S. Pyridine Ligands as Promoters in PdII/0-Catalyzed C–H Olefination Reactions. Org. Lett. 14, 1760-1763, (2012).
32 Emmert, M. H., Cook, A. K., Xie, Y. J. & Sanford, M. S. Remarkably High Reactivity of Pd(OAc)2/Pyridine Catalysts: Nondirected C–H Oxygenation of Arenes. Angew. Chem. Int. Ed. 50, 9409-9412, (2011).
33 Izawa, Y. & Stahl, S. S. Aerobic Oxidative Coupling of o-Xylene: Discovery of 2-Fluoropyridine as a Ligand to Support Selective Pd-Catalyzed C–H Functionalization. Adv. Synth. Catal. 352, 3223-3229, (2010).
34 Wedi, P., Farizyan, M., Bergander, K., Mück-Lichtenfeld, C. & van Gemmeren, M. Mechanism of the Arene-Limited Nondirected C−H Activation of Arenes with Palladium. Angew. Chem. Int. Ed. 60, 15641-15649, (2021).
35 Mondal, A. & van Gemmeren, M. Catalyst-Controlled Regiodivergent C−H Alkynylation of Thiophenes. Angew. Chem. Int. Ed. 60, 742-746 (2021).
36 Farizyan, M., Mondal, A., Mal, S., Deufel, F. & van Gemmeren, M. Palladium-Catalyzed Nondirected Late-Stage C–H Deuteration of Arenes. J. Am. Chem. Soc. 40, 16370–16376, (2021).
37 Chen, H., Farizyan, M., Ghiringhelli, F. & van Gemmeren, M. Sterically Controlled C−H Olefination of Heteroarenes. Angew. Chem. Int. Ed. 59, 12213-12220, (2020).
38 Mondal, A., Chen, H., Flämig, L., Wedi, P. & van Gemmeren, M. Sterically Controlled Late-Stage C–H Alkynylation of Arenes. J. Am. Chem. Soc. 141, 18662-18667, (2019).
39 Chen, H., Wedi, P., Meyer, T., Tavakoli, G. & van Gemmeren, M. Dual Ligand-Enabled Nondirected C−H Olefination of Arenes. Angew. Chem. Int. Ed. 57, 2497-2501, (2018).
40 Sukowski, V., Jia, W.-L., van Diest, R., van Borselen, M. & Fernández-Ibáñez, M. Á. S,O-Ligand-Promoted Pd-Catalyzed C−H Olefination of Anisole Derivatives. Eur. J. Org. Chem. 4132-4135, (2021).
41 Naksomboon, K., Poater, J., Bickelhaupt, F. M. & Fernández-Ibáñez, M. Á. para-Selective C–H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis. J. Am. Chem. Soc. 141, 6719-6725, (2019).
42 Jia, W.-L. et al. Selective C–H Olefination of Indolines (C5) and Tetrahydroquinolines (C6) by Pd/S,O-Ligand Catalysis. Org. Lett. 21, 9339-9342, (2019).
43 Naksomboon, K., Valderas, C., Gómez-Martínez, M., Álvarez-Casao, Y. & Fernández-Ibáñez, M. Á. S,O-Ligand-Promoted Palladium-Catalyzed C–H Functionalization Reactions of Nondirected Arenes. ACS Catal. 7, 6342-6346, (2017).
44 Ramadoss, B., Jin, Y., Asako, S. & Ilies, L. Remote steric control for undirected meta-selective C–H activation of arenes. Science 375, 658-663, (2022).
45 Kuninobu, Y., Ida, H., Nishi, M. & Kanai, M. A meta-selective C–H borylation directed by a secondary interaction between ligand and substrate. Nat. Chem. 7, 712-717, (2015).
46 Gorsline, B. J., Wang, L., Ren, P. & Carrow, B. P. C–H Alkenylation of Heteroarenes: Mechanism, Rate, and Selectivity Changes Enabled by Thioether Ligands. J. Am. Chem. Soc. 139, 9605-9614, (2017).
47 Bruns, D. L., Musaev, D. G. & Stahl, S. S. Can Donor Ligands Make Pd(OAc)2 a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria. J. Am. Chem. Soc. 142, 19678-19688, (2020).
48 Zhao, D., Xu, P. & Ritter, T. Palladium-Catalyzed Late-Stage Direct Arene Cyanation. Chem 5, 97-107, (2019).