10277-56-2Relevant academic research and scientific papers
Stereo- and regioselective thiolysis of 1,2-epoxides in water
Movassagh, Barahman,Soleiman-Beigi, Mohammad
, p. 3239 - 3244 (2007)
A simple, efficient, stereoselective, and highly regioselective procedure for the synthesis of β-hydroxy sulfides by thiolysis of various 1,2-epoxides in water as a solvent, using no catalyst and under very mild conditions, is described. Copyright Taylor
Zn/CeCl3.7H2O-TBPB: A new and 'green' promoter system for rapid and regioselective thiolyzation of 1,2-epoxides with aryl disulfides
Khosropour, Ahmad R.,Khodaei, Mohammad M.,Ghozati, Kazem
, p. 1378 - 1379 (2004)
A new, efficient, clean, and regioselective 'one-pot' procedure for thiolyzation of epoxides with aryl disultides catalyzed by cerium(III) chloride heptahydrate immobilized on tetrabutyl phosphonium bromide as an ionic liquid is reported.
Regioselective reaction of epoxides with disulfides using Zn/AlCl 3 system: A simple synthesis of β-hydroxy sulfides
Movassagh,Sobhani,Kheirdoush,Fadaei
, p. 3103 - 3108 (2003)
Epoxides are regioselectively cleaved by zinc thiolate intermediate, generated from disulfides in the presence of Zn/AlCl3 system, to afford high yields of the corresponding β-hydroxy sulfides.
Tetrabutylammonium fluoride: A powerful catalyst for the regioselective opening of epoxides with thiols
Albanese,Landini,Penso
, p. 34 - 36 (1994)
Tetrabutylammonium fluoride (1) catalyses under mild conditions the opening of epoxides 2a-k with thiols 3-6 to produce the corresponding β-hydroxy thioethers 7-11 in excellent yields (88-100%) and with high regioselectivity. Furthermore, O-protected glyc
Enantioselective S?H Insertion Reactions of α-Carbonyl Sulfoxonium Ylides
Burtoloso, Antonio C. B.,Farrar, Elliot H. E.,Grayson, Matthew N.,Leveille, Alexandria N.,Mattson, Anita E.,Momo, Patrícia B.
, p. 15554 - 15559 (2020)
The first example of enantioselective S?H insertion reactions of sulfoxonium ylides is reported. Under the influence of thiourea catalysis, excellent levels of enantiocontrol (up to 95 percent ee) and yields (up to 97 percent) are achieved for 31 examples
Additive-free thiolysis of epoxides in water: A green and efficient regioselective pathway to β-hydroxy sulfides
Abaee, Saeed M.,Mojtahedi, Mohammad M.,Abbasi, Hassan,Fatemi, Ensieh R.
, p. 282 - 289 (2008)
Room-temperature ring opening of various epoxides with aromatic thiols was carried out in water in the absence of any Lewis acid or additive. High yields of β-hydroxy sulfides with excellent regioselectivity were obtained under very environmentally friend
Efficient, eco-friendly and regioselective method for thiolysis of 1,2-epoxides with diaryl disulfides in the presence of Zn/Bi(TFA) 3-TBPB or Zn/Bi(OTf)3-TBPB
Khosropour, Ahmad R.,Khodaei, Mohammad M.,Ghozati, Kazem
, p. 572 - 576 (2005)
Diaryl disulfides undergo regioselective ring-opening of 1,2-epoxides in the presence of zinc powder and 3-4 mol-% of bismuth(III) trifluoroacetate or 1 mol-% of bismuth(III) triflate in molten tetrabutylphosphonium bromide (TBPB) to afford the correspond
Synthesis and application of Cu(II) immobilized MCM-41 based solid Lewis acid catalyst for aminolysis reaction under solvent-free condition
Chaudhary, Garima,Gupta, Neha,Singh, Amit Pratap
, (2021/07/22)
In this paper, a Cu(II) immobilized periodic mesoporous organosilica (PMOs) was synthesized and used as a reusable solid Lewis acid catalyst for the aminolysis of epoxides under solvent-free conditions. An amide-based ligand, L-propylsilyl (1) having a specific binding pocket was prepared and fabricated on mesoporous MCM-41 to produce mesoporous organosilica L-propylsilyl@MCM-41 (2). Further, it has been utilized for anchoring Cu(II) ions under controlled reaction conditions to yield solid Lewis acid catalyst Cu(II)-L-propylsilyl@MCM-41 (3). The synthesized catalyst 3 exhibits significantly higher catalytic activity for aminolysis compared to hitherto known solid Lewis acid catalysts. An extensive range of β-amino alcohols with high regio and stereoselectivity were prepared by using catalyst 3. The catalyst was recovered easily and reused eight times without any loss in its catalytic activity. Furthermore, the synthesis of clinically significant propranolol (β-blocker) from α- naphthyl glycidyl ether was attained successfully using catalyst 3 in a very decent yield.
Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
Wang, Shun,Cheng, Bei-Yi,Sr?en, Matea,K?nig, Burkhard
supporting information, p. 7524 - 7531 (2020/08/05)
The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.
Biodegradable choline hydroxide promoted environmentally benign thiolysis of epoxides
Azizi, Najmedin,Edrisi, Mahtab
supporting information, p. 525 - 528 (2016/01/20)
An environmentally benign and rapid thiolysis of epoxides using a biodegradable, choline-based task-specific ionic liquid has been developed. The ring opening reaction of aryl and alkyl epoxides proceeded rapidly and afforded the corresponding β-hydroxysulfides in high yields with excellent regioselectivity. The protocol has the advantages of easy work-up, short reaction times, high yields, and a biodegradable catalyst.
