13865-49-1Relevant academic research and scientific papers
THE DIMESITYLBORON GROUP IN ORGANIC SYNTHESIS, IX. A MOST UNUSUAL REACTION : ELECTROPHILIC ATTACK ON SULPHUR IN α-THIOCARBANIONS.
Pelter, Andrew,Bugden, Gina,Pardasani, Ram,Wilson, John
, p. 5033 - 5036 (1986)
Predominant alkylation of a boron-stabilised carbanion containing an α-phenylthio group is unprecedentedly on sulphur rather than carbon.Even in lithium phenylthiomethane a similar effect can be observed, its importance being solvent dependant.
Visible-light-activated selective synthesis of sulfoxides via thiol-ene/oxidation reaction cascade
Singh, Manjula,Yadav, Arvind K.,Yadav, Lal Dhar S.,Singh
, p. 450 - 453 (2018)
A convenient, highly selective and metal-free synthesis of sulfoxides from alkenes and thiols using NHPI as an inexpensive and reusable organophotoredox catalyst is reported. The protocol involves radical thiol-ene/oxidation reaction cascade and utilizes visible light and air (O2) as inexpensive, readily available, non-toxic and eco-sustainable reagents to afford up to 96% yields of the product at room temperature.
Photoinitiated Thiol-Ene “Click” Reaction: An Organocatalytic Alternative
Limnios, Dimitris,Kokotos, Christoforos G.
, p. 323 - 328 (2017)
The thiol-ene coupling (TEC) reaction has attracted a lot of scientific attention during the last years, particularly in the fields of polymers, materials and more recently in drug design. The combination of organocatalysis and photocatalysis has enabled the development of an efficient synergistic protocol for the addition of various thiols to a plethora of olefins. Utilizing phenylglyoxylic acid as the catalyst-initiator and common household bulbs as the light source, we report an organocatalytic photoinitiated TEC reaction showing exceptional tolerance in the presence of various functionalities, untangling previously unsolved problems. (Figure presented.).
Synthesis of new copper(I) based linear 1-D-coordination polymers with neutral imidazolinium-dithiocarboxylate ligands
Neuba,Ortmeyer,Konieczna,Weigel,Fl?rke,Henkel,Wilhelm
, p. 9217 - 9220 (2015)
An imidazolinium-dithiocarboxylate betaine has been applied for the first time as a ligand in a coordination polymer with copper(i) halides. The resulting 1-D-coordination compounds show a linear double chain structure with trigonally coordinated copper(i
Nucleophilic substitution by Grignard reagents on sulfur mustards
Converse, Antonella,Saaidi, Pierre-Loic,Sharpless, K. Barry,Finn
, p. 7336 - 7339 (2004)
With proper activation of the leaving group, sulfur mustards react with Grignard reagents with neighboring group participation of the sulfur atom. 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane is especially useful in this regard, providing clean reactivity with organomagnesium nucleophiles on a topologically constrained scaffold.
Solvent-mediated switching between oxidative addition and addition-oxidation: Access to β-hydroxysulfides and β-arylsulfones by the addition of thiols to olefins in the presence of Oxone
Moorthy, Jarugu Narasimha,Payra, Soumen,Yadav, Navin
, p. 582 - 591 (2022/01/22)
The reaction between aryl olefins and thiols in the presence of Oxone in toluene-water (9:1, v/v) affords β-hydroxy-2-arylethyl aryl sulfides smoothly by the interception of intermediary thiyl radicals with aryl olefins; the former are generated by the ox
Polynuclear heteroleptic ruthenium(II) photoredox catalysts: Evaluation in blue-light-mediated, regioselective thiol-ene reactions
Motimani, Nozuko M.,Ngubane, Siyabonga,Smith, Gregory S.
supporting information, (2021/12/17)
Polynuclear heteroleptic ruthenium(II) photosensitisers combining either imine or amine-functionalised bipyridyl ligands were synthesised (via Schiff-base condensation/reductive amination reactions), characterised and investigated for their photoreactivity in the hydrothiolation reaction. Furthermore, electrochemical, electronic absorption and emission studies of the complexes were conducted. All the ligand-modified, heteroleptic complexes show red-shifted emission spectra (614–633 nm) relative to the canonical [Ru(bpy)3](PF6)2 complex (609 nm), attributed to the transition from the triplet MLCT excited state (3MLCT) to the ground state. The complexes were evaluated as visible-light photoredox catalysts in the radical hydrothiolation reaction of olefins (thiol-ene coupling) to afford thioethers. Control reactions performed in the absence of the photocatalyst resulted in either significantly lower yields (6%) or no product formation, demonstrating the role of the complexes as photoredox catalysts. The reactions carried out using trinuclear complexes (Ered (Ru2+*/+) = +0.300 V vs Ag/Ag+) resulted in increased yields in comparison with their respective mononuclear congeners and greater than those reported for [Ru(bpy)3](PF6)2, demonstrating the benefits of using polynuclear photocatalysts for photoinitiated redox catalysis reactions.
One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
Zupanc, An?e,Jereb, Marjan
, p. 5991 - 6000 (2021/05/05)
This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.
Facile Thiol–Ene Click Protocol Using Benzil as Sensitizer and White LED as Light Source
Das, Anupam,Thomas, K. R. Justin
supporting information, p. 7214 - 7218 (2020/11/30)
The thiol–ene reaction leading to a series of thioether derivatives by simple metal and oxidant free visible light promoted photosensitized protocol, following anti-Markonikov hydrothiolation of unactivated aryl and alkyl olefins at room temperature is demonstrated. Benzil served as a green photosensitizer in this reaction and white LED lights as a light source. This radical based thiol–ene reaction is operationally simple and tolerates a wide variety of functional groups present in olefins.
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
