Deslauriers, R. & Somorjai, R. L. Internal rotations of side chains and backbone in luteinizing hormone-releasing hormone (LH-RH). Analysis of carbon-13 spin-lattice relaxation times. J. Am. Chem. Soc. 98, 1931–1939 (1976).ArticleÂ
PubMedÂ
Google ScholarÂ
Lin, G.-Q., Xu, M.-H., Zhong, Y.-W. & Sun, X.-W. An advance on exploring N-tert-butanesulfinyl imines in asymmetric synthesis of chiral amines. Acc. Chem. Res. 41, 831–840 (2008).ArticleÂ
PubMedÂ
Google ScholarÂ
D’Angelo, N. D. et al. Discovery and optimization of a series of benzothiazole phosphoinositide 3-kinase (PI3K)/mammalian target of rapamycin (mTOR) dual inhibitors. J. Med. Chem. 54, 1789–1811 (2011).ArticleÂ
PubMedÂ
Google ScholarÂ
Jiang, C.-S., Müller, W. E. G., Schröder, H. C. & Guo, Y.-W. Disulfide- and multisulfide-containing metabolites from marine organisms. Chem. Rev. 112, 2179–2207 (2012).ArticleÂ
PubMedÂ
Google ScholarÂ
Omann, L., Königs, C. D. F., Klare, H. F. T. & Oestreich, M. Cooperative catalysis at metal–sulfur bonds. Acc. Chem. Res. 50, 1258–1269 (2017).ArticleÂ
PubMedÂ
Google ScholarÂ
Wang, N., Saidhareddy, P. & Jiang, X. Construction of sulfur-containing moieties in the total synthesis of natural products. Nat. Prod. Rep. 37, 246–275 (2020).ArticleÂ
PubMedÂ
Google ScholarÂ
Kim, J. K., Bonicamp, J. & Caserio, M. C. Methoxymethyl cations. 2. Reactions with allylic ethers and sulfides in the gas phase. J. Org. Chem. 46, 4236–4242 (1981).ArticleÂ
Google ScholarÂ
Mahieu, J.-P., Gosselet, M., Sebille, B. & Beuzard, Y. Synthesis of new thiosulfonates and disulfides from sulfonyl chlorides and thiols. Synth. Commun. 16, 1709–1722 (1986).ArticleÂ
Google ScholarÂ
Chauhan, P., Mahajan, S. & Enders, D. Organocatalytic carbon-sulfur bond-forming reactions. Chem. Rev. 114, 8807–8864 (2014).ArticleÂ
PubMedÂ
Google ScholarÂ
Musiejuk, M. & Witt, D. Recent developments in the synthesis of unsymmetrical disulfanes (disulfides). A review. Org. Prep. Proced. Int. 47, 95–131 (2015).ArticleÂ
Google ScholarÂ
Wu, Q., Zhao, D., Qin, X., Lan, J. & You, J. Synthesis of di(hetero)aryl sulfides by directly using arylsulfonyl chlorides as a sulfur source. Chem. Commun. 47, 9188–9190 (2011).ArticleÂ
Google ScholarÂ
Ge, W. & Wei, Y. Copper(I) iodide catalyzed 3-sulfenylation of indoles with unsymmetric benzothiazolyl-containing disulfides at room temperature. Synthesis 44, 934–940 (2012).ArticleÂ
Google ScholarÂ
Yang, F.-L. & Tian, S.-K. Iodine-catalyzed regioselective sulfenylation of indoles with sulfonyl hydrazides. Angew. Chem. Int. Ed. 52, 4929–4932 (2013).ArticleÂ
Google ScholarÂ
Rao, H. et al. K2S2O8/arenesulfinate: an unprecedented thiolating system enabling selective sulfenylation of indoles under metal-free conditions. RSC Adv. 4, 49165–49169 (2014).ArticleÂ
ADSÂ
Google ScholarÂ
Kumaraswamy, G., Raju, R. & Narayanarao, V. Metal- and base-free syntheses of aryl/alkylthioindoles by the iodine-induced reductive coupling of aryl/alkyl sulfonyl chlorides with indoles. RSC Adv. 5, 22718–22723 (2015).ArticleÂ
ADSÂ
Google ScholarÂ
Liu, C.-R. & Ding, L.-H. Byproduct promoted regioselective sulfenylation of indoles with sulfinic acids. Org. Biomol. Chem. 13, 2251–2254 (2015).ArticleÂ
PubMedÂ
Google ScholarÂ
Weidner, J. P. & Block, S. S. Alkyl and aryl thiolsulfonates. J. Med. Chem. 7, 671–673 (1964).ArticleÂ
PubMedÂ
Google ScholarÂ
Zefirov, N. S., Zyk, N. V., Beloglazkina, E. K. & Kutateladze, A. G. Thiosulfonates: synthesis, reactions and practical applications. Sulfur Rep. 14, 223–240 (1993).ArticleÂ
Google ScholarÂ
Steudel, R. The chemistry of organic polysulfanes R-Sn-R (n > 2). Chem. Rev. 102, 3905–3946 (2002).ArticleÂ
PubMedÂ
Google ScholarÂ
Kim, S., Kim, S., Otsuka, N. & Ryu, I. Tin-free radical carbonylation: thiol ester synthesis using alkyl allyl sulfone precursors, phenyl benzenethiosulfonate, and CO. Angew. Chem. Int. Ed. 44, 6183–6186 (2005).ArticleÂ
Google ScholarÂ
Mampuys, P. et al. Sustainable three-component synthesis of isothioureas from isocyanides, thiosulfonates, and amines. Angew. Chem. Int. Ed. 53, 12849–12854 (2014).ArticleÂ
Google ScholarÂ
Mai, S. & Song, Q. Divergent synthesis of disulfanes and benzenesulfonothioates bearing 2-aminofurans from N-tosylhydrazone-bearing thiocarbamates. Angew. Chem. Int. Ed. 56, 7952–7957 (2017).ArticleÂ
Google ScholarÂ
Javitch, J. A., Li, X., Kaback, J. & Karlin, A. A cysteine residue in the third membrane-spanning segment of the human D2 dopamine receptor is exposed in the binding-site crevice. Proc. Natl Acad. Sci. 91, 10355–10359 (1994).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Gallardo-Godoy, A., Torres-Altoro, M. I., White, K. J., Barker, E. L. & Nichols, D. E. 1-Methylpyridinium-4-(4-phenylmethanethiosulfonate) iodide, MTS-MPP+, a novel scanning cysteine accessibility method (SCAM) reagent for monoamine transporter studies. Bioorg. Med. Chem. 15, 305–311 (2007).ArticleÂ
PubMedÂ
Google ScholarÂ
Sugata, K. et al. Nucleotide-induced flexibility change in neck linkers of dimeric kinesin as detected by distance measurements using spin-labeling EPR. J. Mol. Biol. 386, 626–636 (2009).ArticleÂ
PubMedÂ
Google ScholarÂ
Ge, C. et al. A thiol-thiosulfonate reaction providing a novel strategy for turn-on thiol sensing. Chem. Commun. 51, 14913–14916 (2015).ArticleÂ
Google ScholarÂ
Kutateladze, A. G., Beloglazkina, E. K., Zyk, N. V. & Zefirov, N. S. S-tosylsulfene chloride—the first representative of a new class of sulfene halides. Russ. Chem. Bull. 41, 960–961 (1992).ArticleÂ
Google ScholarÂ
Sotirova, A. et al. The importance of rhamnolipid-biosurfactant-induced changes in bacterial membrane lipids of bacillus subtilis for the antimicrobial activity of thiosulfonates. Curr. Microbiol. 65, 534–541 (2012).ArticleÂ
PubMedÂ
Google ScholarÂ
Selvam, B., Mittal, S. & Shukla, D. Free energy landscape of the complete transport cycle in a key bacterial transporter. ACS Cent. Sci. 4, 1146–1154 (2018).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Ward, D. J., Van de Langemheen, H., Koehne, E., Kreidenweiss, A. & Liskamp, R. M. J. Highly tunable thiosulfonates as a novel class of cysteine protease inhibitors with anti-parasitic activity against Schistosoma mansoni. Bioorg. Med. Chem. 27, 2857–2870 (2019).ArticleÂ
PubMedÂ
Google ScholarÂ
Wang, W., Peng, X., Wei, F., Tung, C.-H. & Xu, Z. Copper(I)-catalyzed interrupted click reaction: synthesis of diverse 5-hetero-functionalized triazoles. Angew. Chem. Int. Ed. 55, 649–653 (2016).ArticleÂ
Google ScholarÂ
Ghiazza, C. et al. Visible-light-mediated metal-free synthesis of trifluoromethylselenolated arenes. Angew. Chem. Int. Ed. 57, 11781–11785 (2018).ArticleÂ
Google ScholarÂ
Li, J., Zhu, D., Lv, L. & Li, C.-J. Radical difluoromethylthiolation of aromatics enabled by visible light. Chem. Sci. 9, 5781–5786 (2018).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Qi, J., Wei, F., Huang, S., Tung, C.-H. & Xu, Z. Copper(I)-catalyzed asymmetric interrupted kinugasa reaction: synthesis of α-thiofunctional chiral β-lactams. Angew. Chem. Int. Ed. 60, 4561–4565 (2021).ArticleÂ
Google ScholarÂ
Xu, B., Wang, D., Hu, Y. & Shen, Q. Silver-catalyzed ring-opening difluoromethylthiolation/trifluoromethylthiolation of cycloalkanols with PhSO2SCF2H or PhSO2SCF3. Org. Chem. Front. 5, 1462–1465 (2018).ArticleÂ
Google ScholarÂ
Dong, Y. et al. Organophotoredox-catalyzed formation of alkyl-aryl and -alkyl C-S/Se bonds from coupling of redox-active esters with thio/selenosulfonates. Org. Lett. 22, 9562–9567 (2020).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Li, J. et al. Visible-light-promoted cross-coupling reactions of 4-Alkyl-1,4-dihydropyridines with thiosulfonate or selenium sulfonate: a unified approach to sulfides, selenides, and sulfoxides. Org. Lett. 22, 4908–4913 (2020).ArticleÂ
PubMedÂ
Google ScholarÂ
Wu, Z. & Pratt, D. A. A divergent strategy for site-selective radical disulfuration of carboxylic acids with trisulfide-1,1-dioxides. Angew. Chem. Int. Ed. 60, 15598–15605 (2021).ArticleÂ
Google ScholarÂ
Zhou, X., Pyle, D., Zhang, Z. & Dong, G. Deacylative thiolation by redox-neutral aromatization-driven C-C fragmentation of ketones. Angew. Chem. Int. Ed. 62, e202213691 (2023).ArticleÂ
Google ScholarÂ
Wu, H. et al. Construction of C-S and C-Se bonds from unstrained ketone precursors under photoredox catalysis. Angew. Chem. Int. Ed. 63, e202314790 (2024).ArticleÂ
Google ScholarÂ
Zhu, D., Shao, X., Hong, X., Lu, L. & Shen, Q. PhSO2SCF2H: a shelf-stable, easily scalable reagent for radical difluoromethylthiolation. Angew. Chem. Int. Ed 55, 15807–15811 (2016).ArticleÂ
Google ScholarÂ
Li, H., Shan, C., Tung, C.-H. & Xu, Z. Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes. Chem. Sci. 8, 2610–2615 (2017).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Gadde, K. et al. Thiosulfonylation of unactivated alkenes with visible-light organic photocatalysis. ACS Catal. 10, 8765–8779 (2020).ArticleÂ
Google ScholarÂ
Peng, Z., Yin, H., Zhang, H. & Jia, T. Regio- and stereoselective photoredox-catalyzed atom transfer radical addition of thiosulfonates to aryl alkynes. Org. Lett. 22, 5885–5889 (2020).ArticleÂ
PubMedÂ
Google ScholarÂ
Lü, S., Wang, Z., Gao, X., Chen, K. & Zhu, S. 1,2-Difunctionalization of acetylene enabled by light. Angew. Chem. Int. Ed. 62, e202300268 (2023).ArticleÂ
Google ScholarÂ
Ren, X. et al. Access to polysulfides through photocatalyzed dithiosulfonylation. Angew. Chem. Int. Ed. 62, e202302199 (2023).ArticleÂ
Google ScholarÂ
Chen, Y. et al. Nickel(ii)/TPMPP catalyzed reductive coupling of oxalates and tetrasulfides: synthesis of unsymmetric disulfides. Org. Chem. Front. 9, 4962–4968 (2022).ArticleÂ
Google ScholarÂ
Wang, F., Chen, Y., Rao, W., Ackermann, L. & Wang, S.-Y. Efficient preparation of unsymmetrical disulfides by nickel-catalyzed reductive coupling strategy. Nat. Commun. 13, 2588 (2022).ArticleÂ
ADSÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Cao, J.-M. et al. Simultaneous preparation of sulfides/selenides and sulfones via synergistic nickel-catalyzed reductive coupling and SN2 reaction. Org. Lett. 25, 9207–9212 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Fujiki, K., Tanifuji, N., Sasaki, Y. & Yokoyama, T. New and facile synthesis of thiosulfonates from sulfinate/disulfide/I2 system. Synthesis 2002, 0343–0348 (2002).ArticleÂ
Google ScholarÂ
Liang, G. et al. NBS-promoted sulfenylation of sulfinates with disulfides leading to unsymmetrical or symmetrical thiosulfonates. Chin. J. Chem. 30, 1611–1616 (2012).ArticleÂ
Google ScholarÂ
Pham, H. T., Nguyen, N.-L. T., Duus, F. & Luu, T. X. T. Ultrasound-accelerated synthesis of asymmetrical thiosulfonate S-esters by base-promoted reaction of sulfonyl chlorides with thiols. Phosphorus Sulfur Silicon Relat. Elem. 190, 1934–1941 (2015).ArticleÂ
Google ScholarÂ
Gui, Y., Qiu, L., Li, Y., Li, H. & Dong, S. Internal activation of peptidyl prolyl thioesters in native chemical ligation. J. Am. Chem. Soc. 138, 4890–4899 (2016).ArticleÂ
PubMedÂ
Google ScholarÂ
Gong, K., Zhou, Y. & Jiang, X. From symmetrical tetrasulfides to trisulfide dioxides via photocatalysis. Green Chem. 23, 9865–9869 (2021).ArticleÂ
Google ScholarÂ
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).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Cheung, K. P. S., Sarkar, S. & Gevorgyan, V. Visible light-induced transition metal catalysis. Chem. Rev. 122, 1543–1625 (2022).ArticleÂ
PubMedÂ
Google ScholarÂ
Bellotti, P. & Glorius, F. Strain-release photocatalysis. J. Am. Chem. Soc. 145, 20716–20732 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Ham, R., Nielsen, C. J., Pullen, S. & Reek, J. N. H. Supramolecular coordination cages for artificial photosynthesis and synthetic photocatalysis. Chem. Rev. 123, 5225–5261 (2023).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Xu, G.-Q., Wang, W. D. & Xu, P.-F. Photocatalyzed enantioselective functionalization of C(sp3)-H bonds. J. Am. Chem. Soc. 146, 1209–1223 (2024).ArticleÂ
PubMedÂ
Google ScholarÂ
He, J. et al. Catalytic decarboxylative radical sulfonylation. Chem 6, 1149–1159 (2020).ArticleÂ
Google ScholarÂ
Mao, R., Balon, J. & Hu, X. Decarboxylative C(sp3)-O cross-coupling. Angew. Chem. Int. Ed. 57, 13624–13628 (2018).ArticleÂ
Google ScholarÂ
Mao, R., Balon, J. & Hu, X. Cross-coupling of alkyl redox-active esters with benzophenone imines: tandem photoredox and copper catalysis. Angew. Chem. Int. Ed. 57, 9501–9504 (2018).ArticleÂ
Google ScholarÂ
Wang, C. et al. Visible-light-driven, copper-catalyzed decarboxylative C(sp3)-H alkylation of glycine and peptides. Angew. Chem. Int. Ed. 57, 15841–15846 (2018).ArticleÂ
ADSÂ
Google ScholarÂ
Dong, X.-Y. et al. A general asymmetric copper-catalysed Sonogashira C(sp3)-C(sp) coupling. Nat. Chem. 11, 1158–1166 (2019).ArticleÂ
PubMedÂ
Google ScholarÂ
Guo, Y., Luo, Y., Mu, S., Xu, J. & Song, Q. Photoinduced decarboxylative phosphorothiolation of N-hydroxyphthalimide esters. Org. Lett. 23, 6729–6734 (2021).ArticleÂ
PubMedÂ
Google ScholarÂ
Tian, Y. et al. A general copper-catalysed enantioconvergent C(sp3)-S cross-coupling via biomimetic radical homolytic substitution. Nat. Chem. 16, 466–475 (2023).ArticleÂ
PubMedÂ
Google ScholarÂ
Mampuys, P. et al. Iodide-catalyzed synthesis of secondary thiocarbamates from isocyanides and thiosulfonates. Org. Lett. 18, 2808–2811 (2016).ArticleÂ
PubMedÂ
Google ScholarÂ
Zhang, Y. et al. Organocatalytic transformation of aldehydes to thioesters with visible light. Chem. Eur. J. 25, 8225–8228 (2019).ArticleÂ
PubMedÂ
Google ScholarÂ
Chen, S. et al. Sandmeyer-type reductive disulfuration of anilines. Org. Lett. 23, 7428–7433 (2021).ArticleÂ
PubMedÂ
Google ScholarÂ
Wang, W., Lin, Y., Ma, Y., Tung, C.-H. & Xu, Z. Cu-catalyzed electrophilic disulfur transfer: synthesis of unsymmetrical disulfides. Org. Lett. 20, 3829–3832 (2018).ArticleÂ
PubMedÂ
Google ScholarÂ
Li, J., Li, M., Duan, X. & Song, W. Copper-catalyzed thiolation of terminal aromatic alkynes to access alkynyl disulfides. Tetrahedron Lett. 61, 152256 (2020).ArticleÂ
Google ScholarÂ
Hunter, R., Kaschula, C., Stellenboom, N., Cotton, J. & Parker, M. I. New excursions into the synthesis and medicinal chemistry of the disulfide bond. Phosphorus Sulfur Silicon Relat. Elem. 188, 1497–1507 (2013).ArticleÂ
Google ScholarÂ
Wang, D., Zhu, N., Chen, P., Lin, Z. & Liu, G. Enantioselective decarboxylative cyanation employing cooperative photoredox catalysis and copper catalysis. J. Am. Chem. Soc. 139, 15632–15635 (2017).ArticleÂ
PubMedÂ
Google ScholarÂ
Zhao, W., Wurz, R. P., Peters, J. C. & Fu, G. C. Photoinduced, copper-catalyzed decarboxylative C-N coupling to generate protected amines: an alternative to the curtius rearrangement. J. Am. Chem. Soc. 139, 12153–12156 (2017).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Xia, H.-D. et al. Photoinduced copper-catalyzed asymmetric decarboxylative alkynylation with terminal alkynes. Angew. Chem. Int. Ed. 59, 16926–16932 (2020).ArticleÂ
Google ScholarÂ
Yi, X., Mao, R., Lavrencic, L. & Hu, X. Photocatalytic decarboxylative coupling of aliphatic N-hydroxyphthalimide esters with polyfluoroaryl nucleophiles. Angew. Chem. Int. Ed. 60, 23557–23563 (2021).ArticleÂ
Google ScholarÂ