Recent trends in direct S-cyanation of thiols

• Mustafa, J.Y. Winum, The importance of sulfur-containing motifs in drug design and discovery. Expert Opin Drug Discov., 17 (2022) 501-512.
• (a) K.A. Scott, J.T. Njardarson, Analysis of US FDA-approved drugs containing sulfur atoms. Curr. Chem., (Z) (2018) 376.

(b) R. J. Mohamed, A. K. O. Aldulaimi, S. A. Aowda, Synthesized of new alkaloid compounds and study their anticancer activity. Paper presented at the AIP Conference Proceedings,  2660 (2022) 020082. doi:10.1063/5.0108821.

(c) A. K. O. Aldulaim, N. M. Hameed, T. A. Hamza, A. S. Abed, The antibacterial characteristics of fluorescent carbon nanoparticles modified silicone denture soft liner. J. Nanostruct., 12 (2022) 774-781. doi:10.22052/JNS.2022.04.001

(d) A. K. O. Aldulaimi, A. H. Idan, A. A. Majhool, M. J. Jawad, Z. H. Khudhair, S. M. Hassan, S. S. S. A. Azziz, Synthesis of new antibiotic agent based on mannich reaction. Int. J. Drug Deliv. Tec., 12(3) (2022) 1428-1432. doi:10.25258/ijddt.12.3.83

(e) M. N. Sidik, Y. Mhd Bakri, S. S. Syed Abdul Azziz, A. K. O. Aldulaimi, C. F. Wong, M. Ibrahim, In silico xanthine oxidase inhibitory activities of alkaloids isolated from alphonsea sp. S. Afr. J. Bot., 147 (2022) 820-825. doi:10.1016/j.sajb.2022.03.024

(f) A. K. O. Aldulaimi, M. J. Jawad, S. M. Hassan, T. S. Alwan, S. S. S. A. Azziz, Y. M. Bakri,. The potential antibacterial activity of a novel amide derivative against gram-positive and gram-negative bacteria. Int. J. Drug Deliv. Tec., 12(2) (2022) 510-515. doi:10.25258/ijddt.12.2.8

(g) A. K. O. Aldulaimi, A. H. Idan, A. H. Radhi, S. A. Aowda, S. S. S. A. Azziz, W. M. N. H. W. Salleh, A. K. O. Aldulaimi, N. A. M. Ali, Gcms analysis and biological activities of iraq zahdi date palm phoenix dactylifera l volatile compositions. Res. J. Pharm. Tec., 13(11) (2020) 5207-5209. doi:10.5958/0974-360X.2020.00910.5

(h) A. K. O. Aldulaimi, A. A. Majhool, I. S. Hasan, M. Adil, S. M. Saeed, A. H. Adhab New MCRs: Preparation of Novel Derivatives of Pyrazoloazepines in Ionic Liquid and Study of Biological Activity, Polycycl. Aromat. Comp., (2023). DOI: 10.1080/10406638.2023.2254903

(i) S. S. S. A., Azziz, A. K. O. Aldulaimi, S. A. Aowda, Y. M. Bakri, A. A. Majhool, R. M. Ibraheem, F. Abdullah, Secondary metabolites from leaves of polyalthia lateriflora and their antimicrobial activity. Int. J.Res. Pharm. Sci. 11(3), (2020) 4353-4358. doi:10.26452/ijrps.v11i3.2652

(j) C. Y. Hsu, A. K. O. Aldulaimi, H. Bahir, A. H. Adhab, S. K. Saraswat, Hydrazinosulfonylation of aryl electrophiles: a straightforward approach for the synthesis of aryl N-aminosulfonamides, RSC adv. 13(27) (2023) 18546-18560.

• S. Sahu, Dual role of organosulfur compounds in foods: a review. J. Environ. Sci. Health., 20 (2002) 61-76.
• (a) K.W. Quasdorf, A.D. Huters, M.W. Lodewyk, D.J. Tantillo, N.K. Garg, Total synthesis of oxidized welwitindolinones and (−)-N-methylwelwitindolinone C isonitrile. Am. Chem. Soc., 134 (2012) 1396-1399; (b) S. Yamamoto, Y. Komiya, A. Kobayashi, R. Minamikawa, T. Oishi, T. Sato, N. Chida, Asymmetric total synthesis of fasicularin by chiral N-alkoxyamide strategy. Org. Lett., 21 (2019) 1868-1871; (c) D.H. Kim, J. Shin, H.J. Kwon, Psammaplin A is a natural prodrug that inhibits class I histone deacetylase. Exp. Mol. Med., 39 (2007) 47-55.
• (a) E. Elhalem, B.N. Bailey, R. Docampo, I. Ujváry, S.H. Szajnman, J.B. Rodriguez, Design, synthesis, and biological evaluation of aryloxyethyl thiocyanate derivatives against Trypanosoma cruzi. Med. Chem., 45 (2002) 3984-3999; (b) R.J. Capon, C. Skene, E.H.T. Liu, E. Lacey, J.H. Gill, K. Heiland, T. Friedel, The isolation and synthesis of novel nematocidal dithiocyanates from an Australian marine sponge, Oceanapia sp. J. Org. Chem., 66 (2001) 7765-7769.
• K. Maurya, A. Mazumder, P.K. Gupta, Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols. Beilstein J. Org. Chem., 13 (2017) 1184-1188.
• R. Prabhu, A.R. Ramesha, S. Chandrasekaran, Reductive dimerization of organic thiocyanates to disulfides mediated by tetrathiomolybdate. J. Org. Chem., 60 (1995) 7142-7143.
• Yang, Z.Y. Tian, C.P. Zhang, Transition‐metal‐free selective synthesis of (Z)‐1,2‐diarylthio‐1‐arylalkenes,(2‐arylethene‐1,1,2‐triyl) tris (arylsulfane)s and alkynyl sulfides from thiocyanates and terminal arylalkynes. ChemistrySelect, 4 (2019) 311-315.
• A. Grieco, Y. Yokoyama, E. Williams, Aryl selenocyanates and aryl thiocyanates: reagents for the preparation of activated esters. J. Org. Chem., 43 (1978) 1283-1285.
• Danoun, B. Bayarmagnai, M.F. Gruenberg, L.J. Goossen, Sandmeyer trifluoromethylthiolation of arenediazonium salts with sodium thiocyanate and Ruppert–Prakash reagent. Chem. Sci., 5 (2014) 1312-1316.
• R. Sardarian, I.D. Inaloo, A.R. Modarresi-Alam, Highly efficient synthesis of alkyl and aryl primary thiocarbamates and dithiocarbamates under metal-and solvent-free conditions. Mol. Divers., 22 (2018) 863-878.
• H. Barton, J.C. Jaszberenyi, E.A. Theodorakis, The invention of radical reactions. Part XXIII new reactions: Nitrile and thiocyanate transfer to carbon radicals from sulfonyl cyanides and sulfonyl isothiocyanates. Tetrahedron, 48 (1992) 2613-2626.
• Castanheiro, J. Suffert, M. Donnard, M. Gulea, Recent advances in the chemistry of organic thiocyanates. Chem. Soc. Rev., 45 (2016) 494-505.
• W. Erian, S.M. Sherif, The chemistry of thiocyanic esters. Tetrahedron, 55 (1999) 7957-8024.
• Selected reviews: (a) A. Hosseinian, S. Ahmadi, F.A.H. Nasab, R. Mohammadi, E. Vessally. Cross-dehydrogenative C–H/S–H coupling reactions. Curr. Chem., 376 (2018) 1-32; (b) W. Peng, E. Vessally, S. Arshadi, A. Monfared, A. Hosseinian, L. Edjlali. Cross-dehydrogenative coupling reactions between C(sp)–H and X–H (X= N, P, S, Si, Sn) bonds: An environmentally benign access to heteroatom-substituted alkynes. Top. Curr. Chem., 377 (2019) 1-22; (c) M. Hamzehloo, A. Hosseinian, S. Ebrahimiasl, A. Monfared, E. Vessally. Direct C-H trifluoromethylthiolation of (hetero) arenes: a review. J. Fluorine Chem., 224 (2019) 52-60; (d) Y. Yang, D. Zhang, E. Vessally. Direct amination of aromatic C–H bonds with free amines. Top. Curr. Chem., 378 (2020) 1-32; (e) Z. He, D. Wu, E. Vessally. Cross-dehydrogenative coupling reactions between formamidic C(sp²)–H and X–H (X= C, O, N) bonds. Top. Curr. Chem., 378 (2020) 1-30; (f) L. Feng, X. Li, B. Liu, E. Vessally. Hydrocarboxylation of alkynes utilizing CO₂ as C1 synthon: a facile and environmentally benign access to α, β-unsaturated carboxylic acids. J. CO₂ Util., 40 (2020) 101220; (g) R.T. Kareem, B. Azizi, M. Asnaashariisfahani, A. Ebadi, E. Vessally. Vicinal halo-trifluoromethylation of alkenes. RSC Adv., 11 (2021) 14941-14955; (h) Y. Cao, N.Y. Xu, A. Issakhov, A.G. Ebadi, M.R.P. Heravi, E. Vessally. Recent advances in direct trifluoromethylselenolation of C–H bonds. J. Fluorine Chem., 252 (2021) 109901; (i) Y. Cao, R. Ahmadi, M.R.P. Heravi, A. Issakhov, A.G. Ebadi, E. Vessally. Recent trends in dehydroxylative trifluoro-methylation,-methoxylation,-methylthiolation, and-methylselenylation of alcohols. RSC Adv., 11 (2021) 39593-39606; (j) Y. Zhang, E. Vessally. Direct halosulfonylation of alkynes: an overview. RSC Adv., 11 (2021) 33447-33460; (k) Y. Cao, S. Soleimani-Amiri, R. Ahmadi, A. Issakhov, A.G. Ebadi, E. Vessally. Alkoxysulfenylation of alkenes: development and recent advances. RSC Adv., 11 (2021) 32513-32525; (l) Y. Cao, S. Abdolmohammadi, R. Ahmadi, A. Issakhov, A.G. Ebadi, E. Vessally. Direct synthesis of sulfenamides, sulfinamides, and sulfonamides from thiols and amines. RSC Adv., 11 (2021) 32394-32407.
• J. Kim, D.H. Kweon, S.D. Cho, H.K. Kim, E.Y. Jung, S.G. Lee, J.R. Falck, Y.J. Yoon, 2-Cyanopyridazin-3 (2H)-ones: Effective and chemoselective electrophilic cyanating agents. Tetrahedron, 61 (2005) 5889-5894.
• Castanheiro, M. Gulea, M. Donnard, J. Suffert, Practical access to aromatic thiocyanates by CuCN‐mediated direct aerobic oxidative cyanation of thiophenols and diaryl disulfides. Eur. J. Org. Chem., (2014) 7814-7817.
• Yamaguchi, K. Sakagami, Y. Miyamoto, X. Jin, N. Mizuno, Oxidative nucleophilic strategy for synthesis of thiocyanates and trifluoromethyl sulfides from thiols. Org. Biomol. Chem., 12 (2014) 9200-9206.
• Jiang, Y. Zhu, H. Li, P. Liu, P. Sun, Direct cyanation of thiophenols or thiols to access thiocyanates under electrochemical conditions. J. Org. Chem., 87 (2022) 10026-10033.
• Wakselman, E. Guibé-Jampel, A. Raoult, W.D. Busse, 1-Cyano-4-dimethylamino-pyridinium salts: new water-soluble reagents for the cyanylation of protein sulphydryl groups. J. Chem. Soc., Chem. Commun., (1976) 21-22.
• Miao, J.P. Tam, Dehydropeptides from orthogonal ligation of unprotected peptides. Org. Lett., 2 (2000) 3711-3713.
• [22] G.D. Pipes, A.A. Kosky, J. Abel, Y. Zhang, M.J. Treuheit, G.R. Kleemann, Optimization and applications of CDAP labeling for the assignment of cysteines. Res., 22 (2005) 1059-1068.
• Q. Wu, D.C. Limburg, D.E. Wilkinson, G.S. Hamilton, 1-Cyanoimidazole as a mild and efficient electrophilic cyanating agent. Org. Lett., 2 (2000) 795-797.
• W. Still, I.D. Watson, An efficient synthetic route to aryl thiocyanates from arenesulfinates. Synth. Commun., 31 (2001) 1355-1359.
• Iranpoor, H. Firouzabadi, H.R. Shaterian, Efficient conversion of thiols to thiocyanates by in situ generated Ph₃P(SCN)₂. Tetrahedron Lett, 43 (2002) 3439-3441.
• Frei, T. Courant, M.D. Wodrich, J. Waser, General and practical formation of thiocyanates from thiols. Chem. Eur. J., 21 (2015) 2662-2668.
• Talavera, J. Pena, M. Alcarazo, Dihalo (imidazolium) sulfuranes: A versatile platform for the synthesis of new electrophilic group-transfer reagents. J. Am. Chem. Soc., 137 (2015) 8704-8707.
• Li, C. Golz, M. Alcarazo, 5‐(Cyano) dibenzothiophenium triflate: A sulfur‐based reagent for electrophilic cyanation and cyanocyclizations. Angew. Chem. Int. Ed., 131 (2019) 9596-9600.
• Li, C. Yang, G. Gao, W. Xia, Na₂S₂O₈ Promoted direct thiocyanates from thiols: a practical method for the synthesis of thiocyanates. Chinese J. Org. Chem., 37 (2017) 480-484.
• Guo, W. Tan, M. Zhao, L. Zheng, K. Tao, D. Chen, X. Fan, Direct photocatalytic S–H bond cyanation with green “CN” source. J. Org. Chem., 83 (2018) 6580-6588.