Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004–2021 (2001).Article
CAS
Google Scholar
Moses, J. E. & Moorhouse, A. D. The growing applications of click chemistry. Chem. Soc. Rev. 36, 1249–1262 (2007).Article
CAS
PubMed
Google Scholar
Devaraj, N. K. & Finn, M. G. Introduction: click chemistry. Chem. Rev. 121, 6697–6698 (2021).Article
CAS
PubMed
Google Scholar
Finn, M. G., Kolb, H. C. & Sharpless, K. B. Click chemistry connections for functional discovery. Nat. Synth. 1, 8–10 (2022).Article
Google Scholar
Huisgen, R. 1,3-Dipolar cycloadditions past and future. Angew. Chem. Int. Ed. 2, 565–632 (1963).Article
Google Scholar
Rostovtsev, V. V., Green, L. G., Fokin, V. V. & Sharpless, K. B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew. Chem. Int. Ed. 41, 2596–2599 (2002).Article
CAS
Google Scholar
Tornøe, C. W., Christensen, C. & Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057–3064 (2002).Article
PubMed
Google Scholar
Meldal, M. & Tornøe, C. W. Cu-catalyzed azide–alkyne cycloaddition. Chem. Rev. 108, 2952–3015 (2008).Article
CAS
PubMed
Google Scholar
Jewett, J. C. & Bertozzi, C. R. Cu-free click cycloaddition reactions in chemical biology. Chem. Soc. Rev. 39, 1272–1279 (2010).Article
CAS
PubMed
PubMed Central
Google Scholar
Bräse, S., Gil, C., Knepper, K. & Zimmermann, V. Organic azides: an exploding diversity of a unique class of compounds. Angew. Chem. Int. Ed. 44, 5188–5240 (2005).Article
Google Scholar
Agard, N. J., Prescher, J. A. & Bertozzi, C. R. A strain-promoted [3 + 2] azide–alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046–15047 (2004).Article
CAS
PubMed
Google Scholar
Manetsch, R. et al. In situ click chemistry: enzyme inhibitors made to their own specifications. J. Am. Chem. Soc. 126, 12809–12818 (2004).Article
CAS
PubMed
Google Scholar
Narayan, S. et al. “On water”: unique reactivity of organic compounds in aqueous suspension. Angew. Chem. Int. Ed. 44, 3275–3279 (2005).Article
CAS
Google Scholar
Baskin, J. M. et al. Copper-free click chemistry for dynamic in vivo imaging. Proc. Natl Acad. Sci. USA 104, 16793–16797 (2007).Article
CAS
PubMed
PubMed Central
Google Scholar
Hoyle, C. E. & Bowman, C. N. Thiol-ene click chemistry. Angew. Chem. Int. Ed. 49, 1540–1573 (2010).Article
CAS
Google Scholar
Kölmel, D. K. & Kool, E. T. Oximes and hydrazones in bioconjugation: mechanism and catalysis. Chem. Rev. 117, 10358–10376 (2017).Article
PubMed
PubMed Central
Google Scholar
Sun, S. et al. Phosphorus fluoride exchange: multidimensional catalytic click chemistry from phosphorus connective hubs. Chem 9, 2128–2143 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Dong, J., Krasnova, L., Finn, M. G. & Sharpless, K. B. Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry. Angew. Chem. Int. Ed. 53, 9430–9448 (2014).Article
CAS
Google Scholar
Zeng, D., Deng, W.-P. & Jiang, X. Linkage chemistry of S(VI) fluorides. Chem. Eur. J. 29, e202300536 (2023).Article
CAS
PubMed
Google Scholar
Zeng, D., Deng, W.-P. & Jiang, X. Advances in the construction of diverse SuFEx linkers. Natl Sci. Rev. 10, nwad123 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Bernús, M. et al. A modular flow platform for sulfur(VI) fluoride exchange ligation of small molecules, peptides and proteins. Nat. Synth. 3, 185–191 (2024).Article
Google Scholar
Zeng, D., Ma, Y., Deng, W.-P., Wang, M. & Jiang, X. The linkage of sulfonimidoyl fluorides and unactivated alkenes via hydrosulfonimidoylation. Angew. Chem. Int. Ed. 61, e202207100 (2022).Article
CAS
Google Scholar
Zhao, S., Zeng, D., Wang, M. & Jiang, X. C-SuFEx linkage of sulfonimidoyl fluorides and organotrifluoroborates. Nat. Commun. 15, 727 (2024).Article
PubMed
PubMed Central
Google Scholar
Teng, S., Shultz, Z. P., Shan, C., Wojtas, L. & Lopchuk, J. M. Asymmetric synthesis of sulfoximines, sulfonimidoyl fluorides and sulfonimidamides enabled by an enantiopure bifunctional S(VI) reagent. Nat. Chem. 16, 183–192 (2024).Article
CAS
PubMed
PubMed Central
Google Scholar
Li, S., Wu, P., Moses, J. E. & Sharpless, K. B. Multidimensional SuFEx click chemistry: sequential sulfur(VI) fluoride exchange connections of diverse modules launched from an SOF4 hub. Angew. Chem. Int. Ed. 56, 2903–2908 (2017).Article
CAS
Google Scholar
Liang, D.-D. et al. Silicon-free SuFEx reactions of sulfonimidoyl fluorides: scope, enantioselectivity, and mechanism. Angew. Chem. Int. Ed. 59, 7494–7500 (2020).Article
CAS
Google Scholar
Peng, Z. et al. Enantioselective sulfur(VI) fluoride exchange reaction of iminosulfur oxydifluorides. Nat. Chem. 16, 353–362 (2024).Article
CAS
PubMed
Google Scholar
Barrow, A. S. et al. The growing applications of SuFEx click chemistry. Chem. Soc. Rev. 48, 4731–4758 (2019).Article
CAS
PubMed
Google Scholar
Li, S. et al. SuFExable polymers with helical structures derived from thionyl tetrafluoride. Nat. Chem. 13, 858–867 (2021).Article
CAS
PubMed
PubMed Central
Google Scholar
Liang, D.-D., Pujari, S. P., Subramaniam, M., Besten, M. & Zuilhof, H. Configurationally chiral SuFEx-based polymers. Angew. Chem. Int. Ed. 61, e202116158 (2022).Article
CAS
Google Scholar
Chao, Y. et al. Sulfur–phenolate exchange: SuFEx-derived dynamic covalent reactions and degradation of SuFEx polymers. Angew. Chem. Int. Ed. 61, e202207456 (2022).Article
CAS
Google Scholar
Lou, T. S.-B. & Willis, M. C. Sulfonyl fluorides as targets and substrates in the development of new synthetic methods. Nat. Rev. Chem. 6, 146–162 (2022).Article
CAS
PubMed
Google Scholar
Hoppmann, C. & Wang, L. Proximity-enabled bioreactivity to generate covalent peptide inhibitors of p53–Mdm4. Chem. Commun. 52, 5140–5143 (2016).Article
CAS
Google Scholar
Yang, B. et al. Proximity-enhanced SuFEx chemical cross-linker for specific and multitargeting cross-linking mass spectrometry. Proc. Natl Acad. Sci. USA 115, 11162–11167 (2018).Article
CAS
PubMed
PubMed Central
Google Scholar
Wang, N. et al. Genetically encoding fluorosulfate‑l‑tyrosine to react with lysine, histidine, and tyrosine via SuFEx in proteins in vivo. J. Am. Chem. Soc. 140, 4995–4999 (2018).Article
CAS
PubMed
PubMed Central
Google Scholar
Zeng, D., Ma, Y., Deng, W.-P., Wang, M. & Jiang, X. Divergent sulfur(VI) fluoride exchange linkage of sulfonimidoyl fluorides and alkynes. Nat. Synth. 1, 455–463 (2022).Article
Google Scholar
Li, S., Wang, N., Yu, B., Sun, W. & Wang, L. Genetically encoded chemical crosslinking of carbohydrate. Nat. Chem. 15, 33–42 (2023).Article
PubMed
Google Scholar
Sun, W. et al. Genetically encoded chemical crosslinking of RNA in vivo. Nat. Chem. 15, 21–32 (2023).Article
CAS
PubMed
Google Scholar
Qin, Z. et al. Discovering covalent inhibitors of protein–protein interactions from trillions of sulfur(VI) fluoride exchange-modified oligonucleotides. Nat. Chem. 15, 1705–1714 (2023).Article
CAS
PubMed
Google Scholar
Li, Q. et al. Developing covalent protein drugs via proximity enabled reactive therapeutics. Cell 182, 85–97 (2020).Article
CAS
PubMed
Google Scholar
Yu, B. et al. Accelerating PERx reaction enables covalent nanobodies for potent neutralization of SARS-CoV-2 and variants. Chem 8, 2766–2783 (2022).Article
CAS
PubMed
PubMed Central
Google Scholar
Homer, J. A. et al. Sulfur fluoride exchange. Nat. Rev. Methods Primers 3, 58 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Ruff, J. K. Sulfur oxyfluoride derivatives. II. Inorg. Chem. 4, 567–570 (1965).Article
CAS
Google Scholar
Meng, G. et al. Modular click chemistry libraries for functional screens using a diazotizing reagent. Nature 574, 86–89 (2019).Article
CAS
PubMed
Google Scholar
Krasheninina, O. A., Thaler, J., Erlacher, M. D. & Micura, R. Amine-to-azide conversion on native RNA via metal-free diazotransfer opens new avenues for RNA manipulations. Angew. Chem. Int. Ed. 60, 6970–6974 (2021).Article
CAS
Google Scholar
Liu, H. et al. Construction of an IMiD-based azide library as a kit for PROTAC research. Org. Biomol. Chem. 19, 166–170 (2021).Article
CAS
PubMed
Google Scholar
Zhang, J. & Dong, J. Modular click chemistry library: searching for better functions. Chin. J. Chem. 39, 1025–1027 (2021).Article
CAS
Google Scholar
Moreno, S., Pittol, J. M. R., Hartl, M. & Micura, R. Robust synthesis of 2′-azido modified RNA from 2′-amino precursors by diazotransfer reaction. Org. Biomol. Chem. 20, 7845–7850 (2022).Article
CAS
PubMed
PubMed Central
Google Scholar
Kofsky, J. M., Daskhan, G. C., Macauley, M. S. & Capicciotti, C. J. Efficient synthesis of azido sugars using fluorosulfuryl azide diazotransfer reagent. Eur. J. Org. Chem. 2022, e202200108 (2022).Article
CAS
Google Scholar
Cui, Q. et al. Discovery of a novel potent antitumor molecule, P19G1, by erlotinib derivative libraries synthesized by modular click-chemistry. Technol. Cancer Res. Treat. 21, 1–14 (2022).Article
Google Scholar
Xin, Y. et al. Affinity selection of double-click triazole libraries for rapid discovery of allosteric modulators for GLP-1 receptor. Proc. Natl Acad. Sci. USA 120, e2220767120 (2023).Article
CAS
PubMed
PubMed Central
Google Scholar
Tian, W. Q. & Wang, Y. A. Mechanisms of Staudinger reactions within density functional theory. J. Org. Chem. 69, 4299–4308 (2004).Article
CAS
PubMed
Google Scholar
Pandiakumar, A. K., Sarma, S. P. & Samuelson, A. G. Mechanistic studies on the diazo transfer reaction. Tetrahedron Lett. 55, 2917–2920 (2014).Article
CAS
Google Scholar
Stevens, M. Y., Sawant, R. T. & Odell, L. R. Synthesis of sulfonyl azides via diazotransfer using an imidazole-1-sulfonyl azide salt: scope and 15N NMR labeling experiments. J. Org. Chem. 79, 4826–4831 (2014).Article
CAS
PubMed
Google Scholar
Gwak, S., Lee, J. H., Kwon, H.-J. & Han, H. A study on the diazo-transfer reaction using o-nitrobenzenesulfonyl azide. Synlett 35, 1429–1435 (2024).CAS
Google Scholar
Fischer, W. & Anselme, J.-P. Reaction of amine anions with p-toluenesulfonyl azide. Novel azide synthesis. J. Am. Chem. Soc. 89, 5284–5285 (1967).Article
CAS
Google Scholar
Nyffeler, P. T., Liang, C.-H., Koeller, K. M. & Wong, C.-H. The chemistry of amine–azide interconversion: catalytic diazotransfer and regioselective azide reduction. J. Am. Chem. Soc. 124, 10773–10778 (2002).Article
CAS
PubMed
Google Scholar
Luy, J.-N. & Tonner, R. Complementary base lowers the barrier in SuFEx click chemistry for primary amine nucleophiles. ACS Omega 5, 31432–31439 (2020).Article
CAS
PubMed
PubMed Central
Google Scholar
Wei, M. et al. A broad-spectrum catalytic amidation of sulfonyl fluorides and fluorosulfates. Angew. Chem. Int. Ed. 60, 7397–7404 (2021).Article
CAS
Google Scholar
Han, B. et al. Calcium bistriflimide-mediated sulfur(VI)–fluoride exchange (SuFEx): mechanistic insights toward instigating catalysis. Inorg. Chem. 61, 9746–9755 (2022).Article
CAS
PubMed
PubMed Central
Google Scholar
Smedley, C. J. et al. Accelerated SuFEx click chemistry for modular synthesis. Angew. Chem. Int. Ed. 61, e202112375 (2022).Article
CAS
Google Scholar
Yang, J.-D., Xue, X.-S., Ji, P., Li, X. & Cheng, J.-P. Internet bond-energy databank (pKa and BDE): iBonD home page. http://ibond.nankai.edu.cn. Accessed Aug 2022.Regitz, M. New methods of preparative organic chemistry. Transfer of diazo groups. Angew. Chem. Int. Ed. 6, 733–749 (1967).Article
CAS
Google Scholar
Goddard-Borger, E. D. & Stick, R. V. An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride. Org. Lett. 9, 3797–3800 (2007).Article
CAS
PubMed
Google Scholar
Kitamura, M., Tashiro, N. & Okauchi, T. 2-Azido-1,3-dimethylimidazolinium chloride: an efficient diazo transfer reagent for 1,3-dicarbonyl compounds. Synlett 18, 2943–2944 (2009).Article
Google Scholar
Samet, M., Buhle, J., Zhou, Y. & Kass, S. R. Charge-enhanced acidity and catalyst activation. J. Am. Chem. Soc. 137, 4678–4680 (2015).Article
CAS
PubMed
Google Scholar
Aragonès, A. C. et al. Electrostatic catalysis of a Diels–Alder reaction. Nature 531, 88–91 (2016).Article
PubMed
Google Scholar
Johnson, C. R., Janiga, E. R. & Haake, M. Chemistry of sulfoxides and related compounds. X. Ylides from salts of sulfoximines. J. Am. Chem. Soc. 90, 3890–3891 (1968).Article
CAS
Google Scholar
Noritake, S., Shibata, N., Nakamura, S., Toru, T. & Shiro, M. Fluorinated Johnson reagent for transfer-trifluoromethylation to carbon nucleophiles. Eur. J. Org. Chem. 2008, 3465–3468 (2008).Article
Google Scholar
Vogel, J. A. et al. Synthesis of highly reactive sulfone iminium fluorides and their use in deoxyfluorination and sulfur fluoride exchange chemistry. Org. Lett. 24, 5962–5966 (2022).Article
CAS
PubMed
Google Scholar
Frisch, M. J. et al. Gaussian 16, Revision C.01 (Gaussian, 2016).Chai, J.-D. & Head-Gordon, M. Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Phys. Chem. Chem. Phys. 10, 6615–6620 (2008).Article
CAS
PubMed
Google Scholar
Weigend, F. & Ahlrichs, R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys. Chem. Chem. Phys. 7, 3297–3305 (2005).Article
CAS
PubMed
Google Scholar
Marenich, A. V., Cramer, C. J. & Truhlar, D. G. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J. Phys. Chem. B 113, 6378–6396 (2009).Article
CAS
PubMed
Google Scholar
Grimme, S. Exploration of chemical compound, conformer, and reaction space with meta-dynamics simulations based on tight-binding quantum chemical calculations. J. Chem. Theory Comput. 15, 2847–2862 (2019).Article
CAS
PubMed
Google Scholar
Riplinger, C. & Neese, F. An efficient and near linear scaling pair natural orbital based local coupled cluster method. J. Chem. Phys. 138, 034106 (2013).Article
PubMed
Google Scholar
Neese, F. The ORCA program system. WIREs Comput. Mol. Sci. 2, 73–78 (2011).Article
Google Scholar
Luchini, G., Alegre-Requena, J. V., Funes-Ardoiz, I. & Paton, R. S. GoodVibes: automated thermochemistry for heterogeneous computational chemistry data [version 1; peer review: 2 approved with reservations]. F1000Res. 9, 291 (2020).Article
Google Scholar
Alecu, I. M., Zheng, J., Zhao, Y. & Truhlar, D. G. Computational thermochemistry: scale factor databases and scale factors for vibrational frequencies obtained from electronic model chemistries. J. Chem. Theory Comput. 6, 2872–2887 (2010).Article
CAS
PubMed
Google Scholar
Li, Y.-P., Gomes, J., Sharada, S. M., Bell, A. T. & Head-Gordon, M. Improved force-field parameters for QM/MM simulations of the energies of adsorption for molecules in zeolites and a free rotor correction to the rigid rotor harmonic oscillator model for adsorption enthalpies. J. Phys. Chem. C 119, 1840–1850 (2015).Article
CAS
Google Scholar
Legault, C. Y. CYLview, 1.0b. http://www.cylview.org (Université de Sherbrooke, 2009).