-Sulfenylsuccinimide/phthalimide: an Alternative Sulfenylating Reagent in Organic Transformations

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2023 Oct 6

PMID 37799175

Authors

Fatemeh Doraghi

Seyedeh Pegah Aledavoud

Mehdi Ghanbarlou

Bagher Larijani

Mohammad Mahdavi

Affiliations

Soon will be listed here.

Abstract

In the field of organosulfur chemistry, sulfenylating agents are an important key in C-S bond formation strategies. Among various organosulfur precursors, -sulfenylsuccinimide/phthalimide derivatives have shown highly electrophilic reactivity for the asymmetric synthesis of many organic compounds. Hence, in this review article, we focus on the application of these alternative sulfenylating reagents in organic transformations.

References

Yu X, Shang Y, Cheng Y, Tian J, Niu Y, Gao W . Synthesis of 4-chalcogenyl pyrazoles via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones. Org Biomol Chem. 2020; 18(9):1806-1811. DOI: 10.1039/d0ob00050g. View

Fontecave M, Ollagnier-de-Choudens S, Mulliez E . Biological radical sulfur insertion reactions. Chem Rev. 2003; 103(6):2149-66. DOI: 10.1021/cr020427j. View

Tian H, Zhu C, Yang H, Fu H . Iron or boron-catalyzed C-H arylthiation of substituted phenols at room temperature. Chem Commun (Camb). 2014; 50(64):8875-7. DOI: 10.1039/c4cc03600j. View

Hostier T, Ferey V, Ricci G, Pardo D, Cossy J . Synthesis of Aryl Sulfides: Metal-Free C-H Sulfenylation of Electron-Rich Arenes. Org Lett. 2015; 17(15):3898-901. DOI: 10.1021/acs.orglett.5b01889. View

Cai Y, Li J, Chen W, Xie M, Liu X, Lin L . Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles. Org Lett. 2012; 14(11):2726-9. DOI: 10.1021/ol3009446. View

Liu L, Stelmach J, Natarajan S, Chen M, Singh S, Schwartz C . SAR of 3,4-dihydropyrido[3,2-d]pyrimidone p38 inhibitors. Bioorg Med Chem Lett. 2003; 13(22):3979-82. DOI: 10.1016/j.bmcl.2003.08.059. View

Li Y, Wei Y, Tian J, Zhang J, Chang H, Gao W . -Thiohydroxy Succinimide Esters (NTSEs): Versatile Reagents for Selective Acyl and Acylthio Transfer. Org Lett. 2022; 24(31):5736-5740. DOI: 10.1021/acs.orglett.2c02160. View

Huang X, Li J, Li X, Wang J, Peng Y, Song G . Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds. RSC Adv. 2022; 9(45):26419-26424. PMC: 9070314. DOI: 10.1039/c9ra05708k. View

Bures J, Isart C, Vilarrasa J . Efficient preparation of N-phenylsulfenyl ketimines from oximes or nitro compounds without racemization of alpha-stereocenters. Org Lett. 2007; 9(22):4635-8. DOI: 10.1021/ol702212n. View

10.

Nalbandian C, Miller E, Toenjes S, Gustafson J . A conjugate Lewis base-Brønsted acid catalyst for the sulfenylation of nitrogen containing heterocycles under mild conditions. Chem Commun (Camb). 2017; 53(9):1494-1497. DOI: 10.1039/c6cc09998j. View

11.

Ghorai J, Kesavan A, Anbarasan P . Cp*Co(III)-catalyzed C2-thiolation and C2,C3-dithiolation of substituted indoles with -(arylthio)succinimide. Chem Commun (Camb). 2021; 57(81):10544-10547. DOI: 10.1039/d1cc03760a. View

12.

Liang Y, Jiao H, Zhang H, Wang Y, Zhao X . Chiral Chalcogenide-Catalyzed Enantioselective Electrophilic Hydrothiolation of Alkenes. Org Lett. 2022; 24(39):7210-7215. DOI: 10.1021/acs.orglett.2c03009. View

13.

Liao K, Zhou F, Yu J, Gao W, Zhou J . Catalytic asymmetric sulfenylation to structurally diverse dithioketals. Chem Commun (Camb). 2015; 51(90):16255-8. DOI: 10.1039/c5cc07010d. View

14.

Eichman C, Stambuli J . Transition metal catalyzed synthesis of aryl sulfides. Molecules. 2011; 16(1):590-608. PMC: 6259452. DOI: 10.3390/molecules16010590. View

15.

Vasquez-Cespedes S, Ferry A, Candish L, Glorius F . Heterogeneously catalyzed direct C-H thiolation of heteroarenes. Angew Chem Int Ed Engl. 2015; 54(19):5772-6. DOI: 10.1002/anie.201411997. View

16.

Denmark S, Chi H . Lewis base catalyzed, enantioselective, intramolecular sulfenoamination of olefins. J Am Chem Soc. 2014; 136(25):8915-8. PMC: 4073881. DOI: 10.1021/ja5046296. View

17.

Li X, Guo Y, Shen Z . Hydrochloric Acid-Promoted Intermolecular 1,2-Thiofunctionalization of Aromatic Alkenes. J Org Chem. 2018; 83(5):2818-2829. DOI: 10.1021/acs.joc.7b03263. View

18.

Markovic I, Stantchev T, Fields K, Tiffany L, Tomic M, Weiss C . Thiol/disulfide exchange is a prerequisite for CXCR4-tropic HIV-1 envelope-mediated T-cell fusion during viral entry. Blood. 2003; 103(5):1586-94. DOI: 10.1182/blood-2003-05-1390. View

19.

Liu G, Huth J, Olejniczak E, Mendoza R, DeVries P, Leitza S . Novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intracellular adhesion molecule-1 interaction. 2. Mechanism of inhibition and structure-based improvement of pharmaceutical properties. J Med Chem. 2001; 44(8):1202-10. DOI: 10.1021/jm000503f. View

20.

Panger J, Denmark S . Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes. Org Lett. 2019; 22(7):2501-2505. PMC: 7127933. DOI: 10.1021/acs.orglett.9b04347. View