Froidevaux, V., Negrell, C., Caillol, S., Pascault, J.-P. & Boutevin, B. Biobased amines: From synthesis to polymers; present and future. Chem. Rev. 116, 14181–14224 (2016).Article
PubMed
Google Scholar
Curran, M. P., Scott, L. J. & Perry, C. M. Cetirizine: a review of its use in allergic disorders. Drugs 64, 523–561 (2004).Article
PubMed
Google Scholar
Farnier, M. Ezetimibe plus fenofibrate: a new combination therapy for the management of mixed hyperlipidaemia? Expert Opin. Pharmacother. 8, 1345–1352 (2007).Article
PubMed
Google Scholar
Li, D.-D., Zhang, Y.-H., Zhang, W. & Zhao, P. Meta-analysis of randomized controlled trials on the efficacy and safety of Donepezil, Galantamine, Rivastigmine, and Memantine for the treatment of Alzheimer’s disease. Front. Neurosci. 13, 472 (2019).Article
PubMed
PubMed Central
Google Scholar
Xie, J.-H., Zhu, S.-F. & Zhou, Q.-L. Transition metal-catalyzed enantioselective hydrogenation of enamines and imines. Chem. Rev. 111, 1713–1760 (2011).Article
PubMed
Google Scholar
Ricci, A. & Bernardi, L. Methodologies in amine synthesis: Challenges and applications. 1st ed. Newark: John Wiley & Sons, Incorporated,Print (2021).Campos, K. R. Direct sp3 C–H bond activation adjacent to nitrogen in heterocycles. Chem. Soc. Rev. 36, 1069–1084 (2007).Article
PubMed
Google Scholar
Mitchell, E. A., Peschiulli, A., Lefevre, N., Meerpoel, L. & Maes, B. U. W. Direct α-functionalization of saturated cyclic amines. Chem. Eur. J. 18, 10092–10142 (2012).Article
PubMed
Google Scholar
Lei, Z., Zhang, W. & Wu, J. Photocatalytic hydrogen atom transfer-induced Arbuzov-type α-C(sp3)–H phosphonylation of aliphatic amines. ACS Catal. 13, 16105–16113 (2023).Article
Google Scholar
Zheng, J. et al. Copper-catalyzed general and selective α-C(sp3)–H silylation of amides via 1,5-hydrogen atom transfer. ACS Catal. 14, 1725–1732 (2024).Article
Google Scholar
Shen, Y., Funez-Ardoiz, I., Schoenebeck, F. & Rovis, T. Site-selective α-C–H functionalization of trialkylamines via reversible hydrogen atom transfer catalysis. J. Am. Chem. Soc. 143, 18952–18959 (2021).Article
PubMed
PubMed Central
Google Scholar
Kaur, J., Barham, J. P. & Site-selective, C. (sp3)–H functionalizations mediated by hydrogen atom transfer reactions via α-amino/α-amido radicals. Synthesis 54, 1461–1477 (2022).Article
Google Scholar
Spangler, J. E., Kobayashi, Y., Verma, P., Wang, D.-H. & Yu, J.-Q. α-Arylation of saturated azacycles and N-methylamines via palladium(II)-catalyzed C(sp3)–H coupling. J. Am. Chem. Soc. 137, 11876–11879 (2015).Article
PubMed
PubMed Central
Google Scholar
Gong, Y., Su, L., Zhu, Z., Ye, Y. & Gong, H. Nickel‐catalyzed thermal redox functionalization of C(sp3)−H bonds with carbon electrophiles. Angew. Chem. Int. Ed. 61, e202201662 (2022).Article
ADS
Google Scholar
Ahneman, D. T. & Doyle, A. G. C–H Functionalization of amines with aryl halides by nickel-photoredox catalysis. Chem. Sci. 7, 7002–7006 (2016).Article
PubMed
PubMed Central
Google Scholar
Shaw, M. H., Shurtleff, V. W., Terrett, J. A., Cuthbertson, J. D. & MacMillan, D. W. C. Native functionality in triple catalytic cross-coupling: sp3 C–H bonds as latent nucleophiles. Science 352, 1304–1308 (2016).Article
ADS
PubMed
PubMed Central
Google Scholar
Gui, Y. Y. et al. Arylation of aniline C(sp3)−H bonds with phenols via an in situ activation strategy. Asian J. Org. Chem. 7, 537–541 (2018).Article
ADS
Google Scholar
Ikeda, Y., Ueno, R., Akai, Y. & Shirakawa, E. α-Arylation of alkylamines with sulfonylarenes through a radical chain mechanism. Chem. Commun. 54, 10471–10474 (2018).Article
Google Scholar
Yonekura, K., Murooka, M., Aoki, K. & Shirakawa, E. Electrochemical direct α-arylation of alkylamines with sulfonylarenes. Org. Lett. 25, 6682–6687 (2023).Article
PubMed
Google Scholar
McNally, A., Prier, C. K. & MacMillan, D. W. C. Discovery of an a-amino C–H arylation reaction using the strategy of accelerated serendipity. Science 334, 1114–1117 (2011).Article
ADS
PubMed
PubMed Central
Google Scholar
Ma, Y. et al. Direct arylation of α‐amino C(sp3)‐H bonds by convergent paired electrolysis. Angew. Chem. Int. Ed. 58, 16548–16552 (2019).Article
Google Scholar
Ueno, R., Ikeda, Y. & Shirakawa, E. tert‐Butoxy‐radical‐promoted α‐arylation of alkylamines with aryl halides. Eur. J. Org. Chem. 28, 4188–4193 (2017).Article
Google Scholar
Qiang, C., Zhang, T., Feng, Z., Liu, P. & Sun, P. Direct amino-α-C−H heteroarylation of amides under electrochemical conditions. Org. Lett. 26, 493–497 (2024).Article
PubMed
Google Scholar
Ide, T. et al. Regio- and chemoselective Csp3–H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis. Chem. Sci. 9, 8453–8460 (2018).Article
PubMed
PubMed Central
Google Scholar
Kobayashi, F. et al. Dual-role catalysis by thiobenzoic acid in Cα–H arylation under photoirradiation. ACS Catal. 11, 82–87 (2021).Article
Google Scholar
Murugesan, K. et al. Photoredox-catalyzed site-selective generation of carbanions from C(sp3)–H bonds in amines. ACS Catal. 12, 3974–3984 (2022).Article
Google Scholar
Chatterjee, J., Rechenmacher, F. & Kessler, H. N-Methylation of peptides and proteins: an important element for modulating biological functions. Angew. Chem. Int. Ed. 52, 254–269 (2003).Article
Google Scholar
Chatterjee, J., Gilon, C., Hoffman, A. & Kessler, H. N-Methylation of peptides: a new perspective in medicinal chemistry. Acc. Chem. Res. 41, 1331–1342 (2008).Article
PubMed
Google Scholar
Barreiro, E. J., Kümmerle, A. E. & Fraga, C. A. M. The methylation effect in medicinal chemistry. Chem. Rev. 111, 5215–5246 (2011).Article
PubMed
Google Scholar
McMurray, L., O’Hara, F. & Gaunt, M. J. Recent developments in natural product synthesis using metal-catalysed C–H bond functionalisation. Chem. Soc. Rev. 40, 1885–1898 (2011).Article
PubMed
Google Scholar
Yamaguchi, J., Yamaguchi, A. D. & Itami, K. C-H Bond functionalization: emerging synthetic tools for natural products and pharmaceuticals. Angew. Chem. Int. Ed. 51, 8960–9009 (2012).Article
Google Scholar
Bellotti, P., Huang, H.-M., Faber, T. & Glorius, F. Photocatalytic late-stage C−H functionalization. Chem. Rev. 123, 4237–4352 (2023).Article
PubMed
Google Scholar
Studer, A. & Bossart, M. Radical aryl migration reactions. Tetrahedron 57, 9649–9667 (2001).Article
Google Scholar
Chen, Z.-M., Zhang, X.-M. & Tu, Y.-Q. Radical aryl migration reactions and synthetic applications. Chem. Soc. Rev. 44, 5220–5245 (2015).Article
ADS
PubMed
Google Scholar
Holden, C. M. & Greaney, M. F. Modern aspects of the Smiles rearrangement. Chem. Eur. J. 23, 8992–9008 (2017).Article
PubMed
Google Scholar
Li, W., Xu, W., Xie, J., Yu, S. & Zhu, C. Distal radical migration strategy: an emerging synthetic means. Chem. Soc. Rev. 47, 654–667 (2018).Article
PubMed
Google Scholar
Huynh, M., De Abreu, M., Belmont, P. & Brachet, E. Spotlight on photoinduced aryl migration reactions. Chem. Eur. J. 27, 3581–3607 (2021).Article
PubMed
Google Scholar
Wu, X., Ma, Z., Feng, T. & Zhu, C. Radical-mediated rearrangements: past, present, and future. Chem. Soc. Rev. 50, 11577–11613 (2021).Article
PubMed
Google Scholar
Allen, A. R., Noten, E. A. & Stephenson, C. R. J. Aryl transfer strategies mediated by photoinduced electron transfer. Chem. Rev. 122, 2695–2751 (2022).Article
PubMed
Google Scholar
Friese, F. W., Mück-Lichtenfeld, C. & Studer, A. Remote C−H functionalization using radical translocating arylating groups. Nat. Commun. 9, 2808 (2018).Article
ADS
PubMed
PubMed Central
Google Scholar
Wu, X. et al. Tertiary‐alcohol‐directed functionalization of remote C(sp3)−H bonds by sequential hydrogen atom and heteroaryl migrations. Angew. Chem. Int. Ed. 57, 1640–1644 (2018).Article
Google Scholar
Wu, X. & Zhu, C. Combination of radical functional group migration (FGM) and hydrogen atom transfer (HAT). Trends Chem. 4, 580–583 (2024).Article
Google Scholar
Kweon, B., Kim, C., Kim, S. & Hong, S. Remote C−H pyridylation of hydroxamates through direct photoexcitation of O-aryl oxime pyridinium intermediates. Angew. Chem. Int. Ed. 60, 26813–26821 (2021).Article
Google Scholar
Sarkar, S., Cheung, K. P. S. & Gevorgyan, V. C–H Functionalization reactions enabled by hydrogen atom transfer to carbon-centered radicals. Chem. Sci. 11, 12974–12993 (2020).Article
PubMed
PubMed Central
Google Scholar
Capaldo, L., Ravelli, D. & Fagnoni, M. Direct photocatalyzed hydrogen atom transfer (HAT) for aliphatic C–H bonds elaboration. Chem. Rev. 122, 1875–1924 (2022).Article
PubMed
Google Scholar
Zhang, J. & Rueping, M. Metallaphotoredox catalysis for sp3 C–H functionalizations through hydrogen atom transfer (HAT). Chem. Soc. Rev. 52, 4099–4120 (2023).Article
PubMed
Google Scholar
Cao, H., Tang, X., Tang, H., Yuan, Y. & Wu, J. Photoinduced intermolecular hydrogen atom transfer reactions in organic synthesis. Chem. Catal. 1, 523–598 (2021).Article
Google Scholar
Bordwell, F. G. Equilibrium acidities in dimethyl sulfoxide solution. Acc. Chem. Res. 21, 456–463 (1988).Article
Google Scholar
Prier, C. K., Rankic, D. A. & MacMillan, D. W. C. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis. Chem. Rev. 113, 5322–5363 (2013).Article
PubMed
PubMed Central
Google Scholar
Leonard, D. J., Ward, J. W. & Clayden, J. Asymmetric α-arylation of amino acids. Nature 562, 105–109 (2018).Article
ADS
PubMed
Google Scholar
Abrams, R. & Clayden, J. Photocatalytic difunctionalization of vinyl ureas by radical addition polar Truce–Smiles rearrangement cascades. Angew. Chem. Int. Ed. 59, 11600–11606 (2020).Article
Google Scholar
Abrams, R., Jesani, M. H., Browning, A. & Clayden, J. Triarylmethanes and their medium‐ring analogues by unactivated Truce–Smiles rearrangement of benzanilides. Angew. Chem. Int. Ed. 60, 11272–11277 (2021).Article
Google Scholar
Wales, S. M., Saunthwal, R. K. & Clayden, J. C(sp3)-Arylation by conformationally accelerated intramolecular nucleophilic aromatic substitution (SNAr). Acc. Chem. Res. 55, 1731–1747 (2022).Article
PubMed
PubMed Central
Google Scholar
Roberts, B. P. Polarity-reversal catalysis of hydrogen-atom abstraction reactions: concepts and applications in organic chemistry. Chem. Soc. Rev. 28, 25–35 (1999).Article
Google Scholar
Ruffoni, A., Mykura, R. C., Bietti, M. & Leonori, D. The interplay of polar effects in controlling the selectivity of radical reactions. Nat. Synth. 1, 682–695 (2022).Article
ADS
Google Scholar
An, Q. Identification of alkoxy radicals as hydrogen atom transfer agents in Ce catalyzed C–H functionalization. J. Am. Chem. Soc. 145, 359–376 (2023).Article
PubMed
Google Scholar
Pulcinella, A., Bonciolini, S., Lukas, F., Sorato, A. & Noël, T. Photocatalytic alkylation of C(sp3)−H bonds using sulfonylhydrazones. Angew. Chem. Int. Ed. 62, e20221537 (2023).Article
Google Scholar
Allart-Simon, I., Gérard, S. & Sapi, J. Radical smiles rearrangement: an update. Molecules 21, 878 (2016).Article
PubMed
PubMed Central
Google Scholar
Whalley, D. M., Seayad, J. & Greaney, M. F. Truce–Smiles rear-rangements by strain release: harnessing primary alkyl radicals for metal‐free arylation. Angew. Chem. Int. Ed. 60, 22219–22223 (2021).Article
Google Scholar
Yan, J. A Radical Smiles rearrangement promoted by neutral Eosin Y as a direct hydrogen atom transfer photocatalyst. J. Am. Chem. Soc. 142, 11357–11362 (2020).Article
PubMed
Google Scholar
Wang, Z.-S. Ynamide Smiles rearrangement triggered by visible-light-mediated regioselective ketyl–ynamide coupling: rapid access to functionalized indoles and isoquinolines. J. Am. Chem. Soc. 142, 3636–3644 (2020).Article
PubMed
Google Scholar
Monos, T. M., MeAtee, R. C. & Stephenson, C. R. J. Arylsulfonyla-cetamides as bifunctional reagents for alkene aminoarylation. Science 361, 1369–1373 (2018).Article
ADS
PubMed
PubMed Central
Google Scholar
Kong, W., Casimiro, M., Merino, E. & Nevado, C. Copper-catalyzed one-pot trifluoromethylation/aryl migration/desulfonylation and C(sp2)–N bond formation of conjugated tosyl amides. J. Am. Chem. Soc. 135, 14480–14483 (2013).Article
PubMed
Google Scholar
Singh, P. P. & Srivastava, V. Recent advances in using 4DPAIPN in photocatalytic transformations. Org. Biomol. Chem. 19, 313–321 (2021).Article
PubMed
Google Scholar
Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press 2007; pp 1-1688.Dénès, F., Pichowicz, M., Povie, G. & Renaud, P. Thiyl radicals in organic synthesis. Chem. Rev. 114, 2587–2693 (2014).Article
PubMed
Google Scholar
Subbaiah, M. A. M. & Meanwell, N. A. Bioisosteres of the phenyl ring: recent strategic applications in lead optimization and drug design. J. Med. Chem. 64, 14046–14128 (2021).Article
PubMed
Google Scholar
Kolk, M. R., van der., Janssen, M. A. C. H., Rutjes, F. P. J. T. & Blanco-Ania, D. Cyclobutanes in small-molecule drug candidates. ChemMedChem 17, e202200020 (2022).Article
PubMed
PubMed Central
Google Scholar
Ilie, S., Alherz, A., Musgrave, C. B. & Glusac, K. D. Thermodynamic and kinetic hydricities of metalFree hydrides. Chem. Soc. Rev. 47, 2809–2836 (2018).Article
Google Scholar
Felpin, F. X. & Lebreton, J. Recent advances in the total synthesis of piperidine and pyrrolidine natural alkaloids with ring‐closing metathesis as a key step. Eur. J. Org. Chem. 20, 3693–3712 (2003).Article
Google Scholar
Bhat, C. Synthetic studies of alkaloids containing pyrrolidine and piperidine structural motifs. ChemistryOpen 4, 192–196 (2015).Article
PubMed
PubMed Central
Google Scholar
Chen, Q.-S., Li, J.-Q. & Zhang, Q.-W. Application of chiral piperidine scaffolds in drug design. Pharm. Fronts 05, e1–e14 (2023).Article
Google Scholar
Shen, Z. et al. General light-mediated, highly diastereoselective piperidine epimerization: from most accessible to most stable stereoisomer. J. Am. Chem. Soc. 143, 126–131 (2021).Article
PubMed
Google Scholar
Clayden, J., Dufour, J., Grainger, D. & Helliwell, M. Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas. J. Am. Chem. Soc. 129, 7488–7489 (2007).Article
PubMed
Google Scholar
Maury, J. & Clayden, J. α-Quaternary proline derivatives by intramolecular diastereoselective arylation of N-carboxamido proline ester enolates. J. Org. Chem. 80, 10757–10768 (2015).Article
PubMed
Google Scholar
Bassan, E. et al. Visible-light driven photocatalytic CO2 reduction promoted by organic photosensitizers and a Mn(I) catalyst. Sustain. Energy Fuels 7, 3454–3463 (2023).Article
Google Scholar
Meng, X., Dong, Y., Liu, Q. & Wang, W. Organophotocatalytic α-deuteration of uunprotected primary amines via H/D exchange with D2O. Chem. Commun. 60, 296–299 (2024).Article
Google Scholar