Direct C–H bond sulfenylation of (Het)arenes using sulfonyl hydrazides as thiol surrogate: a review

References

• Christophersen C, Anthoni U. Organic sulfur compounds from marine organisms. Sulfur Rep. 1986;4:365–442. doi: 10.1080/01961778608082487
   Google Scholar
• Kamel A, Saleh M. Recent studies on the chemistry and biological activities of the organosulfur compounds of garlic (Allium sativum). Stud Nat Prod Chem. 2000;23:455–485. doi: 10.1016/S1572-5995(00)80135-0
   Google Scholar
• Petropoulos S, Di Gioia F, Ntatsi G. Vegetable organosulfur compounds and their health promoting effects. Curr Pharm Des 2017;23:2850–2875. doi: 10.2174/1381612823666170111100531
   Google Scholar
• Scott KA, Njardarson JT. Analysis of US FDA-approved drugs containing sulfur atoms. Top Curr Chem. 2018;376:5. doi: 10.1007/s41061-018-0184-5
   Google Scholar
• Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov. 2011;10:767–777. doi: 10.1038/nrd3554
   Google Scholar
• Devendar P, Yang G-F. Sulfur-containing agrochemicals. Top Curr Chem. 2017;375:82. doi: 10.1007/s41061-017-0169-9
   Google Scholar
• Feng M, Tang B, H Liang S, et al. Sulfur containing scaffolds in drugs: synthesis and application in medicinal chemistry. Curr Top Med Chem. 2016;16:1200–1216. doi: 10.2174/1568026615666150915111741
   Google Scholar
• Kaldor SW, Kalish VJ, Davies JF, et al. Viracept (nelfinavir mesylate, AG1343): a potent, orally bioavailable inhibitor of HIV-1 protease. J Med Chem. 1997;40:3979–3985. doi: 10.1021/jm9704098
   Google Scholar
• D’Agostino A, English CD, Rey JA. Vortioxetine (brintellix): a new serotonergic antidepressant. Pharm Ther. 2015;40:36–40.
   Google Scholar
• Marriner S, Morris D, Dickson B, et al. Pharmacokinetics of albendazole in man. Eur J Clin Pharmacol. 1986;30:705–708. doi: 10.1007/BF00608219
   Google Scholar
• Jacobson JB, Hajman AJ, Wiese J, et al. A new vaginal antifungal agent–butoconazole nitrate. Acta Obstet Gynecol Scand. 1985;64:241–244. doi: 10.3109/00016348509155121
   Google Scholar
• Baron RL. A carbamate insecticide: a case study of aldicarb. Environ Health Perspect. 1994;102:23–27. doi: 10.1289/ehp.94102s1123
   Google Scholar
• Paranjape K, Gowariker V, Krishnamurthy V, et al. The pesticide encyclopedia: Cabi; 2014. ISBN 978-1-78064-014-3.
   Google Scholar
• Melnikov N. Mercaptans, sulfides, and their derivatives. In Chemistry of pesticides. New York: Springer; 1971. p. 240–251.
   Google Scholar
• Madesclaire M. Synthesis of sulfoxides by oxidation of thioethers. Tetrahedron. 1986;42:5459–5495. doi: 10.1016/S0040-4020(01)88150-3
   Google Scholar
• La Sorella G, Sperni L, Strukul G, et al. Supramolecular activation of hydrogen peroxide in the selective sulfoxidation of thioethers by a self-assembled hexameric capsule. Adv Synth Catal. 2016;358:3443–3449. doi: 10.1002/adsc.201600430
   Google Scholar
• Gregori F, Nobili I, Bigi F, et al. Selective oxidation of sulfides to sulfoxides and sulfones using 30% aqueous hydrogen peroxide and silica-vanadia catalyst. J Mol Catal A Chem. 2008;286:124–127. doi: 10.1016/j.molcata.2008.02.004
   Google Scholar
• Miyatake K, Yamamoto K, Endo K, et al. Superacidified reaction of sulfides and esters for the direct synthesis of sulfonium derivatives. J Org Chem. 1998;63:7522–7524. doi: 10.1021/jo980473c
   Google Scholar
• Yang W-C, Wei K, Sun X, et al. Cascade C(sp3)–S bond cleavage and imidoyl C–S formation: radical cyclization of 2-isocyanoaryl thioethers toward 2-substituted benzothiazoles. Org Lett. 2018;20: 3144–3147. doi: 10.1021/acs.orglett.8b01278
   Google Scholar
• Masuya Y, Tobisu M, Chatani N. Palladium-catalyzed synthesis of 2,3-disubstituted benzothiophenes via the annulation of aryl sulfides with alkynes. Org Lett. 2016;18:4312–4315. doi: 10.1021/acs.orglett.6b02055
   Google Scholar
• Kato Y, Miki K, Nishino F, et al. Doyle−Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl) carbenoid transfer. Org Lett. 2003;5:2619–2621. doi: 10.1021/ol034731q
   Google Scholar
• Paun A, Matache M, Enache F, et al. Convenient synthesis of 2-alkynylbenzazoles through Sonogashira cross-coupling reaction between thioethers and terminal alkynes. Tetrahedron Lett. 2015;56:5349–5352. doi: 10.1016/j.tetlet.2015.08.001
   Google Scholar
• Otsuka S, Fujino D, Murakami K, et al. Palladium-catalyzed cross-coupling of unactivated aryl sulfides with arylzinc reagents under mild conditions. Chem Eur J. 2014;20:13146–13149. doi: 10.1002/chem.201404380
   Google Scholar
• Sugahara T, Murakami K, Yorimitsu H, et al. Palladium-catalyzed amination of aryl sulfides with anilines. Angew Chem Int Ed. 2014;53:9329–9333. doi: 10.1002/anie.201404355
   Google Scholar
• Bradshaw JS, South JA, Hales RH. Reaction of the bromo-and fluoronaphthalenes with butyl mercaptide in dimethyl sulfoxide. J Org Chem. 1972;37:2381–2383. doi: 10.1021/jo00980a004
   Google Scholar
• Guindon Y, Frenette R, Fortin R, et al. Direct synthesis of thio ethers from thiols and alcohols. J Org Chem. 1983;48:1357–1359. doi: 10.1021/jo00156a043
   Google Scholar
• Hosseinian A, Nezhad PDK, Ahmadi S, et al. A walk around the decarboxylative C-S cross-coupling reactions. J Sulfur Chem. 2018. doi: 10.1080/17415993.2018.1515314
   Google Scholar
• Monfared A, Ahmadi S, Rahmani Z, et al. Odorless, convenient and one-pot synthesis of thioethers from organic halides and thiourea. J Sulfur Chem. 2018. doi: 10.1080/17415993.2018.1540699
   Google Scholar
• Wang F-X, Zhou S-D, Wang C, et al. N-Hydroxy sulfonamides as new sulfenylating agents for the functionalization of aromatic compounds. Org Biomol Chem. 2017;15:5284–5288. doi: 10.1039/C7OB01390F
   Google Scholar
• Sun P, Yang D, Wei W, et al. Visible light-induced C–H sulfenylation using sulfinic acids. Green Chem. 2017;19:4785–4791. doi: 10.1039/C7GC01891F
   Google Scholar
• Wang TT, Yang FL, Tian SK. Copper-catalyzed sulfenylation of boronic acids with sulfonyl hydrazides. Adv Synth Catal. 2015;357:928–932. doi: 10.1002/adsc.201400995
   Google Scholar
• Guo S-r, He W-m, Xiang J-n, et al. Palladium-catalyzed thiolation of alkanes and ethers with arylsulfonyl hydrazides. ChemComm. 2014;50:8578–8581.
   Google Scholar
• Sun J, Wang Y, Pan Y. Manganese catalysed sulfenylation of N-methyl amides with arenesulfonyl hydrazides. Org Biomol Chem. 2015;13:3878–3881. doi: 10.1039/C5OB00133A
   Google Scholar
• Saini V, Khungar B. Recyclable imidazolium ion-tagged nickel catalyst for microwave-assisted C–S cross-coupling in water using sulfonyl hydrazide as the sulfur source. New J Chem. 2018;42:12796–12801. doi: 10.1039/C8NJ00904J
   Google Scholar
• Ravi C, Semwal R, Kumar R, et al. Iodine-catalyzed one-pot decarboxylative sulfenylation of electron-rich arenes and indoles. ChemSelect. 2018;3:6116–6121.
   Google Scholar
• Shen C, Zhang P, Sun Q, et al. Recent advances in C–S bond formation via C–H bond functionalization and decarboxylation. Chem Soc Rev. 2015;44:291–314. doi: 10.1039/C4CS00239C
   Google Scholar
• Iwasaki M, Nishihara Y. Palladium-catalysed direct thiolation and selenation of aryl C–H bonds assisted by directing groups. Dalton Trans 2016;45:15278–15284. doi: 10.1039/C6DT02167K
   Google Scholar
• Nasab FAH, Fekri LZ, Monfared A, et al. Recent advances in sulfur–nitrogen bond formation via cross-dehydrogenative coupling reactions. RSC Adv. 2018;8:18456–18469. doi: 10.1039/C8RA00356D
   Google Scholar
• Hosseinian A, Ahmadi S, Nasab FAH, et al. Cross-dehydrogenative C–H/S–H coupling reactions. Top Curr Chem 2018;376:39. doi: 10.1007/s41061-018-0217-0
   Google Scholar
• Vessally E, Didehban K, Mohammadi R, et al. Recent advantages in the metal (bulk and nano)-catalyzed S-arylation reactions of thiols with aryl halides in water: a perfect synergy for eco-compatible preparation of aromatic thioethers. J Sulfur Chem. 2018;39:332–349. doi: 10.1080/17415993.2018.1436711
   Google Scholar
• Vessally E, Mohammadi R, Hosseinian A, et al. S-arylation of 2-mercaptobenzazoles: a comprehensive review. J Sulfur Chem. 2018;39:443–463. doi: 10.1080/17415993.2018.1436712
   Google Scholar
• Hosseinian A, Zare Fekri L, Monfared A, et al. Transition-metal-catalyzed C–N cross-coupling reactions of N-unsubstituted sulfoximines: a review. J Sulfur Chem 2018. doi: 10.1080/17415993.2018.1471142
   Google Scholar
• Vessally E, Edjlali L, Hosseinian A, et al. Novel routes to quinoline derivatives from N-propargylamines. RSC Adv. 2016;6:49730–49746. doi: 10.1039/C6RA05221E
   Google Scholar
• Arshadi S, Vessally E, Sobati M, et al. Chemical fixation of CO2 to N-propargylamines: a straightforward route to 2-oxazolidinones. J CO₂ Util. 2017;19:120–129. doi: 10.1016/j.jcou.2017.03.009
   Google Scholar
• Hosseinian A, Farshbaf S, Mohammadi R, et al. Advancements in six-membered cyclic carbonate (1, 3-dioxan-2-one) synthesis utilizing carbon dioxide as a C1 source. RSC Adv 2018;8:17976–17988. doi: 10.1039/C8RA01280F
   Google Scholar
• Sarhandi S, Daghagheleh M, Vali M, et al. New insight in Hiyama cross-coupling reactions: Decarboxylative, denitrogenative and desulfidative couplings. Chem Rev Lett. 2018;1:9–15.
   Google Scholar
• Daghagheleh M, Vali M, Rahmani Z, et al. A review on the CO2 Incorporation Reactions Using Arynes, Chem Rev Lett. 2018;1:23–30.
   Google Scholar
• Shahidi S, Farajzadeh P, Ojaghloo P, et al. Nanocatalysts for conversion of aldehydes/alcohols/amines to nitriles: A review, Chem Rev Lett. 2018;1:37–44.
   Google Scholar
• Mohammadi S, Musavi M, Abdollahzadeh F, et al. Application of Nanocatalysts in C-Te Cross-Coupling Reactions: An Overview, Chem Rev Lett. 2018;1:49–55.
   Google Scholar
• Farshbaf S, Sreerama L, Khodayari T, et al. Propargylic ureas as powerful and versatile building blocks in the synthesis of various key medicinal heterocyclic compounds, Chem Rev Lett. 2018;1:56–67.
   Google Scholar
• Hosseinian A, Farshbaf S, Fekri L Z, et al. Cross-Dehydrogenative Coupling Reactions Between P(O)–H and X–H (X = S, N, O, P) Bonds, Top Curr Chem., 2018;376:23–42. doi: 10.1007/s41061-018-0200-9
   Google Scholar
• Farshbaf S, Zare Fekri L, Nikpassand M, et al. Dehydrative condensation of ß-aminoalcohols with CO2: An environmentally benign access to 2-oxazolidinone derivatives, J CO₂ Util. 2018;25:194–204. doi: 10.1016/j.jcou.2018.03.020
   Google Scholar
• Rahaman R, Devi N, Sarma K, et al. Microwave-assisted synthesis of 3-sulfenylindoles by sulfonyl hydrazides using organic ionic base-Brønsted acid. RSC Adv. 2016;6:10873–10879. doi: 10.1039/C5RA24851E
   Google Scholar
• Raghuvanshi DS, Verma N. Regioselective thiolation of electron rich arenes and heterocycles in recyclable catalytic media. RSC Adv. 2017;7:22860–22868. doi: 10.1039/C7RA02350B
   Google Scholar
• Yang FL, Tian SK. Iodine-catalyzed regioselective sulfenylation of indoles with sulfonyl hydrazides. Angew Chem Int Ed 2013;52:4929–4932. doi: 10.1002/anie.201301437
   Google Scholar
• Kang X, Yan R, Yu G, et al. Iodine-mediated thiolation of substituted naphthols/naphthylamines and arylsulfonyl hydrazides via C(sp2)–H bond functionalization. J Org Chem. 2014;79:10605–10610. doi: 10.1021/jo501778h
   Google Scholar
• Bagdi AK, Mitra S, Ghosh M, et al. Iodine-catalyzed regioselective thiolation of imidazo [1, 2-a] pyridines using sulfonyl hydrazides as a thiol surrogate. Org Biomol Chem 2015;13:3314–3320. doi: 10.1039/C5OB00033E
   Google Scholar
• Zhao X, Zhang L, Lu X, et al. Synthesis of 2-aryl and 3-aryl benzo[b]furan thioethers using aryl sulfonyl hydrazides as sulfenylation reagents. J Org Chem. 2015;80:2918–2924. doi: 10.1021/acs.joc.5b00146
   Google Scholar
• Zhao W, Xie P, Bian Z, et al. Ammonium iodide induced nonradical regioselective sulfenylation of flavones via a C–H functionalization process. J Org Chem. 2015;80:9167–9175. doi: 10.1021/acs.joc.5b01602
   Google Scholar
• Zhao X, Deng Z, Wei A, et al. Iodine-catalysed regioselective thiolation of flavonoids using sulfonyl hydrazides as sulfenylation reagents. Org Biomol Chem. 2016;14:7304–7312. doi: 10.1039/C6OB01006G
   Google Scholar
• Zhao X, Li T, Zhang L, et al. Iodine-catalyzed thiolation of electron-rich aromatics using sulfonyl hydrazides as sulfenylation reagents. Org Biomol Chem. 2016;14:1131–1137. doi: 10.1039/C5OB02193F
   Google Scholar
• Pang X, Xiang L, Yang X, et al. Iodine-mediated synthesis of aromatic thioethers with aromatic amines and sulfonyl hydrazides in high regioselectivity via C(sp2)-H bond functionalization. Adv Synth Catal. 2016;358:321–325. doi: 10.1002/adsc.201500943
   Google Scholar
• Liu W, Wang S, Cai Z, et al. Iodine-catalyzed regioselective sulfenylation of 4H-pyrido [1, 2-a] pyrimidin-4-ones with sulfonyl hydrazides. Synlett. 2018;29:116–120. doi: 10.1055/s-0036-1588549
   Google Scholar
• Yang Z, Yan Y, Li A, et al. Iodine-mediated sulfenylation of 4-hydroxycoumarins with sulfonyl hydrazides under aqueous conditions. New J Chem. 2018;42:14738–14741. doi: 10.1039/C8NJ03461C
   Google Scholar
• Li X, Xu Y, Wu W, et al. Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio-and stereoselective synthesis of sulfones and thioethers. Chem Eur J. 2014;20:7911–7915. doi: 10.1002/chem.201402815
   Google Scholar
• Paul S, Shrestha R, Edison T, et al. Copper (I) bromide-dimethyl sulfide-catalyzed direct sulfanylation of 4-hydroxycoumarins and 4-hydroxyquinolinones with arylsulfonylhydrazides and selective fluorescence switch-on sensing of cadmium (II) ion in water. Adv Synth Catal. 2016;358:3050–3056. doi: 10.1002/adsc.201600429
   Google Scholar
• Chen L, Liu P, Wu J, et al. Cu-catalyzed direct C-H thiolation of electron-rich arenes with arylsulfonyl hydrazides. Tetrahedron. 2018;74:1513–1519. doi: 10.1016/j.tet.2018.02.014
   Google Scholar
• Yu Q, Yang Y, Wan J-P, et al. Copper-catalyzed C5–H sulfenylation of unprotected 8-aminoquinolines using sulfonyl hydrazides. J Org Chem. 2018;83:11385–11391. doi: 10.1021/acs.joc.8b01658
   Google Scholar
• Guo J-Y, Dai R-H, Xu W-C, et al. TfNHNHBoc as a SCF3 source for the sulfenylation of indoles. ChemComm. 2018;54:8980–8982.
   Google Scholar
• Nookaraju U, Begari E, Yetra RR, et al. Cecl3⋅7H2O-NaI promoted regioselective sulfenylation of indoles with sulfonylhydrazides. ChemSelect. 2016;1:81–85.
   Google Scholar
• Yang Y, Zhang S, Tang L, et al. Catalyst-free thiolation of indoles with sulfonyl hydrazides for the synthesis of 3-sulfenylindoles in water. Green Chem. 2016;18:2609–2613. doi: 10.1039/C6GC00313C
   Google Scholar
• Chowdhury SR, Fadikar P, Ul Hoque I, et al. Catalyst-free regioselective sulfenylation of imidazoheterocycles with sulfonyl hydrazides in water. Asian J Org Chem. 2018;7:332–336. doi: 10.1002/ajoc.201700670
   Google Scholar