Electron-transfer initiated nucleophilic substitution of thiophenolate anion by 1-chloro-substituted 4-(thiazol-2-ylazo)naphthalenes
Tài liệu tham khảo
Iversen, 1974, Electrolytic generation of nucleophiles. IV. Reductive alkylation and acylation of disulfides, Acta Chem. Scand., 28, 827, 10.3891/acta.chem.scand.28b-0827
Christensen, 1997, Investigation of the direct and indirect reduction processes of some disulfides by electrochemical means, Acta Chem. Scand., 51, 307, 10.3891/acta.chem.scand.51-0307
Daasbjerg, 1999, Evidence for large inner reorganization energies in the reduction of diaryl disulfides: toward a mechanistic link between concerted and stepwise dissociative electron transfers?, J. Am. Chem. Soc., 121, 1750, 10.1021/ja983374p
Borsari, 2003, Electrochemical behaviour of diphenyl disulfide and thiophenol on glassy carbon and gold electrodes in aprotic media, Electroanalysis, 15, 1192, 10.1002/elan.200390146
Danehy, 1961, The alkaline decomposition of organic disulfides. I. Some dithiodicarboxylic acids, J. Am. Chem. Soc., 83, 1109, 10.1021/ja01466a026
Ma, 2016, Efficient synthesis of unsymmetrical heteroaryl thioethers and chalcogenides by alkali hydroxide-mediated SNAr reactions of heteroaryl halides and dichhalcogenides, RSC Adv., 6, 56930, 10.1039/C6RA10517C
Taniguchi, 2017, Transition-metal-free and oxidant-free cross-coupling of arylhydrazines with disulfides: base-promoted synthesis of unsymmetrical aryl sulphides, J. Org. Chem., 82, 6647, 10.1021/acs.joc.7b00767
Kumar, 2013, Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulphides and selenides from aryl bromides, Tetrahedron, 69, 5383, 10.1016/j.tet.2013.04.113
Barham, 2016, KOtBu: a privileged reagent for electron transfer reactions?, J. Am. Chem. Soc., 138, 7402, 10.1021/jacs.6b03282
Han, 2016, A metal-free diverse synthesis of difluoromethylthioethers and difluorobis(arylthio)methanes from RSX (X = SR, Cl, SO2Ph) and TMSCF2H, J. Org. Chem., 81, 2506, 10.1021/acs.joc.6b00089
Kumar, 2016, Regioselective transition metal- and halogen-free direct dithiolation at C(sp3)–H of nitrotoluenes with diaryl disulfides, Org. Biomol. Chem., 14, 9210, 10.1039/C6OB01856D
Wang, 2014, Silver-mediated decarboxylative C−S cross-coupling of aliphatic carboxylic acids under mild conditions, Org. Lett., 16, 4586, 10.1021/ol502144c
Yang, 2014, Silver-mediated oxidative vinylic C-H bond sulfenylation of enamides with disulfides, Org. Biomol. Chem., 12, 9519, 10.1039/C4OB01970A
Zhang, 2015, Silver-catalyzed direct thiolation of quinones by activation of aryl disulfides to synthesize quinonyl aryl thioethers, J. Org. Chem., 80, 4919, 10.1021/acs.joc.5b00247
Antonello, 2002, Theoretical and electrochemical analysis of dissociative electron transfers proceeding through formation of loose radical anion species: reduction of symmetrical and unsymmetrical disulfides, J. Am. Chem. Soc., 124, 7529, 10.1021/ja012545e
Antonello, 2003, Formation and cleavage of aromatic disulfide radical anions, J. Am. Chem. Soc., 125, 14905, 10.1021/ja036380g
Yu, 2019, Preparation of RS-substituted 1-(thiazo-2-ylazo)-naphthalenes by nucleophilic substitution of chlorine with mercaptans, Eur. J Org. Chem., 1317–1329
E. Dmitrieva, A. Popov, X. Yu, H. Hartmann, in press.
Terrier, 2013, Modern Nucleophilic Aromatic Substitution, Wiley-VCH, Weinheim
Pietra, 1969, Mechanisms for nucleophilic and photonucleophilic aromatic substitution reactions, Quarterly Rev., 23, 504, 10.1039/qr9692300504
Tillett, 1969, Reaction mechanisms, Ann. Rep. Progr. Chem., Sect. B: Org. Chem. 66, 59, 10.1039/oc9696600059
Makosza, 2017, How does nucleophilic aromatic substitution in nitroarenes really proceed: general mechanism, Synthesis, 49, 3247, 10.1055/s-0036-1588444
Makosza, 2011, Nucleophilic substitution of hydrogen in nitroarenes: a new chapter of aromatic chemistry, Synthesis, 15, 2341, 10.1055/s-0030-1260668
van Zwet, 1965, Aromatic diazothio-ethers, Chem. Comm. London, 14, 313, 10.1039/c19650000313
Sakla, 1974, Preparation of diazo phenyl sulphides. Kinetics and mechanism of the diazo coupling reaction of p-nitrobenzenediazo phenyl sulphide with ß-naphthol under various conditions, Helv. Chim. Acta, 57, 481, 10.1002/hlca.19740570222
Holy, 1971, Radical anion intermediates in organic chemistry, Angew. Chem. Int. Ed., 10, 115, 10.1002/anie.197101151
Heinze, 1984, Cyclic voltammetry – “Electrochemical Spectroscopy”, Angew. Chem. Int. Ed., 23, 831, 10.1002/anie.198408313
Fry, 2005, Disproportionation of arene radical anions is driven overwhelming by solvation, not ion pairing, Electrochem. Commun., 7, 602, 10.1016/j.elecom.2005.04.007
Fry, 2006, A computational study of solution effects on the disproportionation of electrochemically generated polycyclic aromatic hydrocarbon radical anions. Thermodynamics and structure, Tetrahedron, 62, 6558, 10.1016/j.tet.2006.03.057
Bondarchuk, 2018, Spontaneous disproportionation of lithium biphenyl in solution: a combined experimental and theoretical study, New J. Chem., 42, 5168, 10.1039/C7NJ04726F
Xiao, 2017, Piperidine promoted direct sulfenylation of 2-naphthol with aryl thiols under aqueous conditions, Chem. Select, 2, 428