- Electrochemical oxidations of thioethers: Modulation of oxidation potential using a hydrogen bonding network
-
A highly efficient chemo-selective electrochemical oxidation of thioethers to sulfoxides and sulfones was developed. The hydrogen bonding network generated from hexafluoro-2-propanol (HFIP) and acetic acid (AcOH) plays an important role in the modulation of oxidation potential. The hydrogen bonding network complexes strongly with the sulfoxide, making it less prone to further oxidation. Therefore, thioethers can be selectively electrochemically oxidized to sulfoxides and over-oxidization could be minimized. Moreover, this modulation of oxidization via hydrogen bonding was supported by density functional theory (DFT) calculations and cyclic voltammetry experiments.
- Liu, Shiwen,Chen, Bocheng,Yang, Yi,Yang, Yuhao,Chen, Qianjin,Zeng, Xiaojun,Xu, Bo
-
-
- Electrochemical synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide
-
A new route for a one-pot synthesis of methyl sulfoxides from thiophenols/thiols and dimethyl sulfoxide using an electrochemical technique was developed. This protocol proceeded smoothly by employing electrons and hydrogen peroxide as clean oxidants, and a wide range of aromatic and aliphatic sulfoxides were synthesized in moderate to good yields.
- Du, Ke-Si,Huang, Jing-Mei
-
supporting information
p. 1405 - 1411
(2018/03/27)
-
- An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor
-
A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The procedure exhibits a broad scope and good functional group compatibility providing access to various sulfoxides (15 examples), sulfones (15 examples) and disulfides (6 examples). The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry.
- Laudadio, Gabriele,Straathof, Natan J. W.,Lanting, Menno D.,Knoops, Benny,Hessel, Volker,No?l, Timothy
-
p. 4061 - 4066
(2017/09/07)
-
- Supramolecular Activation of Hydrogen Peroxide in the Selective Sulfoxidation of Thioethers by a Self-Assembled Hexameric Capsule
-
An efficient metal-free organocatalytic activation of hydrogen peroxide (H2O2) towards thioethers leading to the corresponding sulfoxides in high yields at room temperature within hours was promoted by the hexameric capsule formed by
- La Sorella, Giorgio,Sperni, Laura,Strukul, Giorgio,Scarso, Alessandro
-
p. 3443 - 3449
(2016/11/13)
-
- Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine
-
An efficient and practical catalytic method for the aerobic oxidative transformation of sulfides into sulfoxides, and thiols into disulfides with formic acid/TEA in the presence of a new, readily available, and stable flavin catalyst 5d is described. This journal is the Partner Organisations 2014.
- Murahashi, Shun-Ichi,Zhang, Dazhi,Iida, Hiroki,Miyawaki, Toshio,Uenaka, Masaaki,Murano, Kenji,Meguro, Kanji
-
supporting information
p. 10295 - 10298
(2014/08/18)
-
- Oxidation of organic sulfides by imidazolium fluorochromate: A kinetic and mechanistic approach
-
The oxidation of organic sulfides by imidazolium fluorochromate resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to imidazolium fluorochromate. A Michaelis-Menten type kinetics was observed with respect t
- Mathur, Lokesh,Choudhary,Prakash, Om,Sharma, Pradeep K.
-
p. 2597 - 2603
(2014/06/09)
-
- Oxidation of organic sulfides by tetraethylammonium chlorochromate: A kinetic and mechanistic study
-
The oxidation of organic sulfides by tetraethylammonium chlorochromate (TEACC) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both TEACC and the sulfide. The reaction is catalyzed by toluene-p-sulfon
- Sharma, Deepika,Pancharia,Vadera,Sharma, Pradeep K.
-
experimental part
p. 315 - 326
(2012/01/04)
-
- Kinetics and mechanism of the oxidation of organic sulfides with bis(pyridine)silver permanganate
-
The oxidation of organic sulfides by bis(pyridine)silver permanganate (BPSP) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both BPSP and sulfides. The reaction is catalysed by hydrogen ions. The rat
- Banerji, Jayshree,Banerji,Kotai, Laszlo,Sharma, Deepika,Sharma, Pradeep K.
-
scheme or table
p. 1879 - 1886
(2012/04/04)
-
- Kinetics and mechanism of the oxidation of some organic sulfides by morpholinium chlorochromate
-
The oxidation of organic sulfides by morpholinium chlorochromate (MCC) resulted in the formation of the corresponding sulfoxides. The reaction is first order with respect to both MCC and the sulfide. The reaction is catalyzed by toluene-p-sulfonic acid (T
- Malani, Neha,Baghmar, Manju,Sharma, Pradeep K.
-
experimental part
p. 65 - 72
(2009/04/07)
-
- Kinetics and mechanism of the oxidation of organic sulphides by quinolinium bromochromate
-
The oxidation of thirty-four sulphides by quinolinium bromochromate (QBC) has been found to result in the formation of the corresponding sulphoxides. The reaction is first order with respect to both QBC and the sulphide. The reaction is catalysed by hydro
- Dhariwal, Varsha,Yajurvedi, Deeksha,Sharma, Pradeep K.
-
p. 1158 - 1164
(2007/10/03)
-
- Binding of hydrophobic hydroxamic acids enhances peroxidase's stereoselectivity in nonaqueous sulfoxidations
-
Horseradish peroxidase exhibits a meager stereoselectivity (E) in the sulfoxidation of thioanisole (1a) in 99.8% (v/v) methanol. The E value, however, is greatly enhanced when the enzyme forms a complex with benzohydroxamic acid (2a). These findings are rationalized by means of molecular dynamics simulations and energy minimization which correctly explain (i) why the free enzyme is not stereoselective, (ii) why 2a inhibits peroxidase-catalyzed sulfoxidation of 1a but the enzymatic formation of one enantiomer of the sulfoxide product is inhibited much more than that of the other, thereby raising peroxidase's E, and (iii) why in the presence of 2a the enzyme favors production of the S sulfoxide of 1a. The generality of the observed ligand-induced stereoselectivity enhancement is demonstrated with other hydrophobic hydroxamic acids, as well as with additional thioether substrates.
- Das, Prasanta Kumar,Caaveiro, Jose M.M.,Luque, Susana,Klibanov, Alexander M.
-
p. 782 - 787
(2007/10/03)
-
- Kinetics and mechanism of the oxidation of organic sulfides by quinolinium fluorochromate
-
The oxidation of organic sulfides by quinolinium fluorochromate (QFC), to the corresponding sulfoxides, is first order with respect to QFC. Michaelis-Menten type kinetics were observed with respect to the sulfide. The correlation analyses of the rate of t
- Bhandari, Abhinav,Sharma, Pradeep. K.,Banerji, Kalyan K.
-
p. 653 - 675
(2007/10/03)
-
- Kinetics and correlation analysis of reactivity in oxidation of organic sulfides by hexamethylenetetramine-bromine
-
The oxidation of organic sulfides by hexamethylenetetramine-bromine (HABR) to the corresponding sulfoxides is first order with respect to HABR. Michaelis-Menten-type kinetics were observed with respect to the sulfide. It is proposed that HABR itself is th
- Choudhary, Kirti,Suri, Deepa,Kothari, Seema,Banerji, Kalyan K.
-
p. 283 - 292
(2007/10/03)
-
- Kinetics and Mechanism of the Oxidation of Organic Sulfides by Bis(2,2′-bipyridyl)copper(II) Permanganate
-
The oxidation of 34 sulfides by bis(2,2′-bipyridyl)copper(II) permanganate (BBCP) resulted in the formation of the corresponding sulfoxide. The reaction is first order with respect to BBCP. Michaelis-Menten type kinetics were observed with respect to the
- Bohra, Anupama,Sharma, Pradeep K.,Banerji, Kalyan K.
-
p. 3562 - 3567
(2007/10/03)
-
- Kinetics and Mechanism of the Oxidation of Organic Sulfides by Pyridinium Bromochromate
-
The oxidation of thirty-four sulfides by pyridinium bromochromate (PBC) resulted in the formation of the corresponding sulfoxides.The reaction is first order with respect to both PBC and the sulfide.The oxidation was studied in 19 different solvents.An an
- Loonker, Kavita,Sharma, Pradeep K.,Banerji, Kalyan K.
-
p. 1262 - 1285
(2007/10/03)
-
- Chloroperoxidase and hydrogen peroxide: An efficient system for enzymatic enantioselective sulfoxidations
-
High enantioselectivities were obtained in chloroperoxidase catalyzed oxidation of organic sulfides (99% ee in the case of methyl 2-pyridyl sulfide) with H2O2 in aqueous buffer solution, pH 5, at 25°C. The kinetic parameters in the oxidation of a series of sulfides both with H2O2 and tert-butyl hydroperoxide were determined and the data are consistent with enzymatic oxidation involving presumably a ternary complex. In all cases the reaction afforded the (R) sulfoxide as predominant or exclusive enantiomer.
- Colonna,Gaggero,Casella,Carrea,Pasta
-
-
- A MODEL FOR FAD-CONTAINING MONOOXYGENASE : THE OXYDATION OF THIOANISOLE DERIVATES BY AN ISOALLOXAZINE HYDROPEROXIDE
-
A 4a-isoalloxazine hydroperoxide oxidizes thioanisole derivates to corresponding sulfoxides by a mechanism which involves nucleophilic attack of sulfur on electrophilic oxygen.
- Miller, Audrey
-
p. 753 - 756
(2007/10/02)
-