42330-81-4Relevant articles and documents
Photoredox β-thiol-α-carbonylation of enones accompanied by unexpected Csp2-C(CO) bond cleavage
Du, Ding,Feng, Jie,Ma, Rui,Zhang, Beichen,Zhang, Kuili
supporting information, p. 7549 - 7553 (2020/10/13)
An olefinic difunctionalization method of enones was presented hereviaaerobic visible-light catalysis. A novel reactivity was showcased in conjunction with the selective Csp2-C(CO) bond activation of enones, which provided a convenient method for the preparation of various β-thiolated-α-functionalized compounds. Moreover, the preliminary investigation of the mechanism indicated that a β-peroxysulfide intermediate was formed under the promotion of visible light under an oxygen atmosphere, which finally induced the unexpected C-C bond cleavage.
Addition of unactivated thiols to epoxides and oxetanes catalyzed by a rhenium-oxo complex
Badiceanu, Alexandra D.,Garst, Alyson E.,Trubitt, Meredith E.,Nolin, Kristine A.
, p. 67 - 70 (2014/03/21)
A method for synthesizing β- and γ-hydroxy thioethers via addition of unactivated thiols to epoxides and oxetanes has been developed. This reaction is proposed to proceed through an unconventional mode of activation of the heterocycles. The transformation is catalyzed by ReO2I(PPh 3)2 affording β- and γ-hydroxy thioethers in moderate to excellent yield with excellent regioselectivity.
Erbium(III) triflate is a highly efficient catalyst for the synthesis of β-alkoxy alcohols, 1,2-diols and β-hydroxy sulfides by ring opening of epoxides
Dalpozzo, Renato,Nardi, Monica,Oliverio, Manuela,Paonessa, Rosina,Procopio, Antonio
experimental part, p. 3433 - 3438 (2010/02/28)
Chemo- and stereoselectivity in the ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields.
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 (2007/10/03)
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
BiCl3 catalyzed thiolyzation reaction of 1,2-epoxides with diaryl disulfides in the presence of zinc powder and ionic liquid
Khosropour,Khodaei,Ghozati
, p. 2525 - 2531 (2007/10/03)
A new and efficient method has been developed for the regio- and chemoselective synthesis of β-hydroxysulfides with the ring-opening reaction of 1,2-epoxides by diaryl disulfides and zinc powder in the presence of a catalytic amount of BiCl3 in
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 (2007/10/03)
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.
The generation of (Samarium) thiolates from aryl thiocyanates and their reaction with epoxides: A route to β-hydroxy sulfides
Still, Ian W.J.,Martyn, L. James P.
, p. 913 - 923 (2007/10/03)
This investigation describes the reduction of an aryl thiocyanate with samarium(II) iodide, followed by reaction with various epoxides, to produce β-hydroxy sulfides. This method of ring opening of epoxides provides a substantial improvement in reaction time and convenience over existing methods while maintaining good regioselectivity and excellent yield.
Additive Pummerer reactions of vinylic sulfoxides. Synthesis of γ-hydroxy-α,β-unsaturated esters, α-hydroxyketones, and 2-phenylsulfenyl aldehydes and primary alcohols
Craig, Donald,Daniels, Kevin,MacKenzie, A. Roderick
, p. 11263 - 11304 (2007/10/02)
Treatment of β-monosubstituted vinylic sulfoxides 1 with trifluoroacetic anhydride in dichloromethane gave excellent yields of 1,2-bis(trifluoroacetoxy)thioethers 6. Mildly basic methanolysis of 2-alkyl-substituted 6 gave α-hydroxyaldehydes 11 as monomer-dimer mixtures; similar treatment of the 2-aryl analogues afforded aryl (hydroxymethyl) ketones 12. Compounds 11 underwent Wittig reactions with methoxycarbonylmethylenetriphenylphosphorane to give high yields of γ-hydroxy-α,β-unsaturated esters 13, predominantly as the E-isomers. β-Monosubstituted vinylic sulfoxides 1 possessing a β-aryl group, and β-disubstituted vinylic sulfoxides 3 reacted with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride to give 2-(phenylsulfenyl) acylals 14. These gave 2-phenylsulfenyl aldehydes 15 upon basic methanolysis, and the corresponding primary alcohols 16 on reduction with sodium borohydride. Reaction of both geometric isomers of enantiomerically pure vinylic sulfoxide 1o with TFAA gave racemic 6o as a mixture of diastereomers. Reaction of optically pure (E)- and (Z)-1p with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride gave acylal 19 in 10.5 and 23% e.e., respectively.
