References
- Nohara T, Fujiwara Y, Ikeda T, et al. Cyclic sulfoxides garlicnins B2, B3, B4, C2, and C3 from allium sativum. Chem Pharm Bull. 2013;61:695–699.
- Ilardi EA, Vitaku E, Njardarson JT. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery. J Med Chem. 2014;57:2832–2842.
- Trost BM, Rao M. Development of chiral sulfoxide ligands for asymmetric catalysis. Angew Chem Int Ed. 2015;54:5026–5043.
- Melone L, Punta C. Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review. Beilstein J Org Chem. 2013;9:1296–1310.
- Ishii Y, Sakaguchi S, Iwahama T. Innovation of hydrocarbon oxidation with molecular oxygen and related reactions. Adv Synth Catal. 2001;343:393–427.
- Recupero F, Punta C. Free radical functionalization of organic compounds catalyzed by N–hydroxyphthalimide. Chem Rev. 2007;107:3800–3842.
- Koshino N, Saha B, Espenson JH. Kinetic study of the phthalimide N-oxyl radical in acetic acid. Hydrogen abstraction from substituted toluenes, benzaldehydes, and benzyl alcohols. J Org Chem. 2003;68:9364–9370.
- Amorati R, Lucarini M, Mugnaini V, et al. Hydroxylamines as oxidation catalysts: thermochemical and kinetic studies. J Org Chem. 2003;68:1747–1754.
- Bietti M, Lanzalunga O, Lapi A, et al. Aerobic oxidation of 4–alkyl-N,N-dimethylbenzylamines catalyzed by N-hydroxyphthalimide. Protonation driven control over regioselectivity. J Org Chem. 2017;82:5761–5768.
- Bietti M, Forcina V, Lanzalunga O, et al. Kinetic study of the reaction of the phthalimide-N-oxyl radical with amides: structural and medium effects on the hydrogen atom transfer reactivity and selectivity. J Org Chem. 2016;81:11924–11931.
- Barbieri A, Lanzalunga O, Lapi A, et al. N-hydroxyphthalimide: a hydrogen atom transfer (HAT) mediator in hydrocarbon oxidations promoted by nonheme iron(IV)-oxo complexes. J Org Chem. 2019;84:13549–13556.
- Di Berto Mancini M, Del Gelsomino A, Di Stefano S, et al. Change of selectivity in C-H functionalization promoted by nonheme iron(IV)-oxo complexes by the effect of the N-hydroxyphthalimide HAT mediator. ACS Omega. 2021;6:26428–26438.
- Capraro MG, Franchi P, Lanzalunga O, et al. Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations. J Org Chem. 2014;79:6435–6443.
- Masui M, Hara S, Ueshima T, et al. Anodic oxidation of compounds having benzylic or allylic carbon and α-carbon to heteroatom using N-hydroxyphthalimide as a mediator. Chem Pharm Bull. 1983;31:4209–4211.
- Ueda C, Noyama M, Ohmori H, et al. Reactivity of phthalimide-N-oxyl: a kinetic study. Chem Pharm Bull. 1987;35:1372–1377.
- Iwahama T, Sakaguchi S, Ishii Y. Selective oxidation of sulfides to sulfoxides with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) in the presence of alcohols. Tetrahedron Lett. 1998;39:9059–9062.
- Del Giacco T, Lanzalunga O, Lapi A, et al. Photosensitized oxidation of aryl benzyl sulfoxides. evidence for nucleophilic assistance to the c-s bond cleavage of aryl benzyl sulfoxide radical cations. J Org Chem. 2015;80:2310–2318.
- Micha-Screttas M, Screttas CG. Preparation of alkyl phenyl sulfides by electrophilically catalyzed displacement of certain nucleophiles by thiophenoxy Group1. J Org Chem. 1977;42:1462–1465.
- Lapi A, D’Alfonso C, Del Giacco T, et al. Competition between Cα-S and Cα-Cβ bond cleavage in β-hydroxysulfoxides cation radicals generated by photoinduced electron transfer. Photochem Photobiol. 2021;97:1310–1321.
- Baciocchi E, Lanzalunga O, Marconi F. The mechanism of enzymatic and biomimetic oxidations of aromatic sulfides and sulfoxides. Tetrahedron Lett. 1994;35:9771–9774.
- Darmanyan AP, Gregory DD, Guo Y, et al. Generation and decay of aryl sulfinyl and sulfenyl radicals: a transient absorption and computational study 1. J Phys Chem A. 1997;101:6855–6863.
- Chang MY, Cheng YC, Chan CK. A route to benzylic arylsulfoxides from β-ketosulfoxides. Tetrahedron. 2016;72:4068–4075.
- Nam W, Lee YM, Fukuzumi S. Tuning reactivity and mechanism in oxidation reactions by mononuclear nonheme iron(IV)-Oxo complexes. Acc Chem Res. 2014;47:1146–1154.
- Yoshihito W, Shigeru O, Takashi I. Mechanisms of enzymatic S-oxygenation of thioanisole derivatives and O-demethylation of anisole derivatives promoted by both microsomes and a reconstituted system with purified cytochrome P-450. Bull Chem Soc Jpn. 1982;55:188–195.
- Kobayashi S, Nakano M, Kimura T, et al. On the mechanism of the peroxidase-catalyzed oxygen-transfer reaction. Biochemistry. 1987;26:5019–5022.
- Coniglio A, Galli C, Gentili P, et al. Hydrogen atom abstraction from C-H bonds of benzylamides by the aminoxyl radical BTNO: a kinetic study. Org Biomol Chem. 2009;7:155–160.
- Lu X, Li XX, Lee YM, et al. Electron-transfer and redox reactivity of high-valent iron imido and oxo complexes with the formal oxidation states of five and six. J Am Chem Soc. 2020;142:3891–3904.
- Brown HC, Okamoto Y. Electrophilic substituent constants. J Am Chem Soc. 1958;80:4979–4987.
- Lakk-Bogáth D, Csonka R, Speier G, et al. Formation, characterization, and reactivity of a nonheme oxoiron(IV) complex derived from the chiral pentadentate ligand AsN4Py. Inorg Chem. 2016;55:10090–10093.
- A similar ( value (−1.5) was found by Kobayashi in the oxidation of thioanisoles promoted by horseradish peroxidase (HRP) where an electron mechanism was proposed to occur from the sulfide to the active species iron-oxo complex (Compound I) formed after reaction of the HRP resting state with H2O2.25 Higher ρ values were reported by Neuman et al. for the one electron oxidation of thioanisoles promoted by a V-Mo complex (−3.6)31 and by Srinivasan et al. for the one-electron oxidation of thioanisoles promoted by Cr(VI) (−2.1)32.
- Khenkin AM, Leitus G, Neumann R. Electron transfer-oxygen transfer oxygenation of sulfides catalyzed by the H5PV2Mo10O40 polyoxometalate. J Am Chem Soc. 2010;132:11446–11448.
- Srinivasan C, Chellamani A, Rajagopal S. Mechanism of the oxidation of alkyl aryl and diphenyl sulfides by chromium(VI). J Org Chem. 1985;50:1201–1205.
- A much more negative value of the slope (−10.5) was observed in the sulfoxidation of thioanisoles catalyzed by a high-valent iron-oxo species in heme enzymes where the reaction proceeded through an electron-transfer pathway34.
- Goto Y, Matsui T, Ozaki SI, et al. Mechanisms of sulfoxidation catalyzed by high-valent intermediates of heme enzymes: electron-transfer vs oxygen-transfer mechanism. J Am Chem Soc. 1999;121:9497–9502.
- Mazzonna M, Bietti M, Dilabio GA, et al. Importance of π-stacking interactions in the hydrogen atom transfer reactions from activated phenols to short-lived N-oxyl radicals. J Org Chem. 2014;79:5209–5218.
- D’Alfonso C, Bietti M, DiLabio GA, et al. Reactions of the phthalimide N–oxyl radical (PINO) with activated phenols: the contribution of π–stacking interactions to hydrogen atom transfer rates. J Org Chem. 2013;78:1026–1037.
- Baciocchi E, Bietti M, Di Fusco M, et al. A kinetic study of the electron-transfer reaction of the phthalimide-N-oxyl radical (PINO) with ferrocenes. J Org Chem. 2007;72:8748–8754.
- Bonesi SM, Manet I, Freccero M, et al. Photosensitized oxidation of sulfides: discriminating between the singlet-oxygen mechanism and electron transfer involving superoxide anion or molecular oxygen. Chem Eur J. 2006;12:4884–4857.
- Bonesi SM, Fagnoni M, Albini A. Photosensitized electron transfer oxidation of sulfides: a steady-state study. Eur J Org Chem. 2008: 2612–2620.
- Bonesi SM, Fagnoni M, Albini A. Photosensitized electron transfer oxidation of sulfides: structure and medium effect. J Sulfur Chem. 2008;29:367–376.
- Barbieri A, Del Giacco T, Di Stefano S, et al. Electron transfer mechanism in the oxidation of aryl 1–methyl-1-phenylethyl sulfides promoted by nonheme iron(IV)-oxo complexes: the rate of the oxygen rebound process. J Org Chem. 2016;81:12382–12387.
- Barbieri A, De Carlo Chimienti R, Del Giacco T, et al. Oxidation of aryl diphenylmethyl sulfides promoted by a non-heme iron(IV)-oxo complex: evidence for electron transfer-oxygen transfer mechanism. J Org Chem. 2016;81:2513–2520.
- Baciocchi E, Gerini MF, Del Giacco T, et al. Rates of C-S bond cleavage in t-alkyl phenyl sulfide radical cations. Org Lett. 2006;8:641–644.
- Lanzalunga O. C-S bond cleavage in aromatic sulfide radical cations. Phosphorus Sulfur Silicon. 2013;188:322–330.
- Lanzalunga O, Lapi A. Recent photo- and radiation chemical studies of sulfur radical cations. J Sulfur Chem. 2012;33:101–129.
- Baciocchi E, Bettoni M, Del Giacco T, et al. Structure and C-S bond cleavage in aryl 1-methyl-1-arylethyl sulfide radical cations. J Org Chem. 2011;76:573–582.