51755-92-1Relevant academic research and scientific papers
Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant
Kupwade,Khot,Lad,Desai,Wadgaonkar
, p. 6875 - 6888 (2017/10/06)
Abstract: We describe here our journey from the failure of our attempts in controlled oxidation of sulfides to sulfoxides using an Oxone–KBr combination to our success in the development of a catalyst-free protocol for the oxidation of sulfides to sulfoxides using Oxone as an oxidant. We also describe the failure of our attempts at the oxidation of sulfides to sulfones using an excess of Oxone–KBr as well as Oxone, and our success towards the development of a rapid, scalable and chromatography-free protocol for the oxidation of sulfides to sulfones using diethylamine–Oxone as an unprecedented catalyst–oxidant combination.
Iodine-Triggered Aerobic Oxysulfonylation of Styrenes
Choudhuri, Khokan,Achar, Tapas Kumar,Mal, Prasenjit
, p. 3566 - 3576 (2017/10/24)
An iodine-triggered dioxygen activation in oxysulfonylation reactions of unactivated olefins using sulfonyl hydrazides and iodine as catalyst is reported here. In one pot, near quantitative syntheses of β-hydroxysulfones were achieved at 70 °C, within 7 h, in acetonitrile and under aerobic conditions. A plausible mechanism is established by radical trapping and 18O labelling experiments for the operationally simple, efficient and economically viable transformation. The direct activation of aerial oxygen under metal-free and mild conditions is proposed for the oxysulfonylation of olefins. (Figure presented.).
One-pot synthesis of β-hydroxysulfones and its application in the preparation of anticancer drug bicalutamide
Wang, Yajun,Jiang, Wei,Huo, Congde
, p. 10628 - 10634 (2018/05/31)
An efficient one-pot multistep strategy has been developed, comprising auto-oxidative difunctionalization of alkenes, oxidation of sulfides, and a further reduction of peroxides for the synthesis of complex β-hydroxysulfone derivatives from phenthiols and alkenes. This method has several advantageous characteristics, including readily available substrates, low-cost and environmental benign reagents, nontoxic and renewable solvents, and mild reaction conditions. The application of this transformation to the multigram-scale preparation of the anticancer drug bicalutamide is accomplished.
Visible-Light-Promoted Remote C-H Functionalization of o-Diazoniaphenyl Alkyl Sulfones
Du, Shaofu,Kimball, Elizabeth Ann,Ragains, Justin R.
, p. 5553 - 5556 (2017/10/25)
Visible-light irradiation of ortho-diazoniaphenyl alkyl sulfones in the presence of Ru(bpy)32+ results in remote Csp3-H functionalization. Key mechanistic steps in these processes involve intramolecular hydrogen atom transfer from Csp3-H bonds to aryl radicals to generate alkyl/benzyl radicals. Subsequent polar crossover occurs by single-electron oxidation of the alkyl/benzyl radicals to carbenium ions that then intercept nucleophiles. We have developed remote hydroxylations, etherifications, an amidation, and C-C bond formation processes using this strategy.
(E)-Specific direct Julia-olefination of aryl alcohols without extra reducing agents promoted by bases
Yao, Chuan-Zhi,Li, Qiang-Qiang,Wang, Mei-Mei,Ning, Xiao-Shan,Kang, Yan-Biao
supporting information, p. 7729 - 7732 (2015/05/12)
An unprecedented base-promoted direct olefination of aryl alcohols with sulfones via a Julia-type reaction has been described. No extra reductants are needed for Julia reaction since alcohols work as double sources of aldehydes and the hydride. Generally high yields were given for both terminal and highly (E)-selective internal olefins.
Aerobic Nickel-Catalyzed Hydroxysulfonylation of Alkenes Using Sodium Sulfinates
Taniguchi, Nobukazu
, p. 7797 - 7802 (2015/08/18)
Nickel-catalyzed hydroxysulfonylation of alkenes was achieved using sodium sulfinates under air atmosphere. The procedure enabled the selective synthesis of β-hydroxysulfones in good yields and suppressed the formation of β-ketosulfones. On the contrary, sulfonylation of alkynes with sodium sulfonates afforded only β-ketosulfones.
Molecular-iodine-catalyzed aerobic oxidative synthesis of β-hydroxy sulfones from alkenes
Kariya, Atsumasa,Yamaguchi, Tomoaki,Nobuta, Tomoya,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
, p. 12191 - 12194 (2014/04/03)
The synthesis of β-hydroxy sulfones from alkenes and sodium sulfinates under aerobic oxidative conditions was achieved in the presence of a catalytic amount of molecular iodine. Molecular oxygen in air serves as the terminal oxidant and the catalytic amount of molecular iodine acts as the sulfonyl radical initiator and peroxide reductant. This journal is the Partner Organisations 2014.
Catalytic asymmetric conjugate boration of α,β-unsaturated sulfones
Moure, Abraham L.,Gomez Arrayas, Ramon,Carretero, Juan C.
, p. 6701 - 6703 (2011/07/30)
The α,β-unsaturated sulfones are suitable activated olefins in catalytic asymmetric conjugate β-boration. These substrates undergo smooth conjugate addition of bis(pinacolato)diboron [B2(pin)2] catalyzed by nonracemic CuI-diphosphine complexes to provide, upon subsequent oxidation, β-hydroxy sulfones in good yields and high enantiocontrol.
A method for the conversion of sulfoximines to sulfones: Application to polymer-bound sulfoximines and to the synthesis of chiral sulfones
Hachtel, Jochen,Gais, Hans-Joachim
, p. 1457 - 1465 (2007/10/03)
Reaction of N-alkyl, N-aryl, and N-H sulfoximines with m- chloroperbenzoic acid cleanly gives the corresponding sulfones in high yield. In the case of the cleavage of N-alkyl and N-arylsulfoximines, formation of the corresponding nitroso compounds as the other reaction product was proven. Starting from enantio- and diastereopure sulfoximines, a number of chiral sulfones, including the axially chiral sulfone 6 and the sulfonyl- functionalized homoallylic alcohol 8, have been prepared. Reaction of the enantiopure sulfoximine 30 with Merrifield resin gave the polymer-bound sulfoximine 32. Oxidative cleavage of 32 afforded the sulfone 16 in high yield. Deprotonation of the sulfoximine resin 32 and reaction of Li-32 with benzaldehyde and propanal furnished the β-hydroxysulfoximine resins 33a and 33b, respectively. Oxidative cleavage of 33a and 33b readily afforded the β- hydroxy sulfones 14a and 14b, respectively.
