- Production of dynamic lipid bilayers using the reversible thiol-thioester exchange reaction
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Thiol lysolipids undergo thiol-thioester exchange with two phenyl thioester-functionalized tails to produce phospholipid structures that assemble into liposomes with differences in exchange rates, temperature sensitivity, permeability, and continued excha
- Konetski, Danielle,Mavila, Sudheendran,Wang, Chen,Worrell, Brady,Bowman, Christopher N.
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supporting information
p. 8108 - 8111
(2018/07/29)
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- Equilibrium shift in the rhodium-catalyzed acyl transfer reactions
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Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio) pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes.
- Arisawa, Mieko,Igarashi, Yui,Kobayashi, Haruki,Yamada, Toru,Bando, Kentaro,Ichikawa, Takuya,Yamaguchi, Masahiko
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supporting information; experimental part
p. 7846 - 7859
(2011/10/12)
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- Odorless diphenyl diselenide and disulfide: Syntheses and applications
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Bis[4-(trimethylsilyl)phenyl]diselenide (3) and bis[4-(trimethylsilyl) phenyl]disulfide (31) are found to be odorless equivalents of the commonly used diphenyl diselenide and diphenyl disulfide, respectively. The diselenide 3 is shown to be useful in the preparation of odorless selenium(II) chloride 26 and selenium(IV) trichloride 28 that follow similar reactivity patterns to their phenyl derivatives and can be stored refrigerated under dry conditions. The corresponding selenium(II) bromide had to be prepared fresh from 3 before use. It is also shown that the trimethylsilyl group in the sulfide products can be protodesilylated quantitatively using TFA. Georg Thieme Verlag Stuttgart.
- Patra, Pranab K.,Shanmugasundaram, Kandasamy,Matoba, Manabu,Nishide, Kiyoharu,Kajimoto, Tetsuya,Node, Manabu
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p. 447 - 457
(2007/10/03)
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- Reductive cleavage of the sulfur-sulfur bond by the samarium/Cp 2TiCI2 used for the synthesis of S-phenyl thiolesters
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A mild method is reported for the reductive cleavage of the sulfur-sulfur bond by the samarium/ Cp2TICI2 system to give a phenylthiolate anion species which reacts with acyl chlorides to give the corresponding S-phenyl thiolesters in
- Jia, Xueshun,Zhang, Yongmin
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p. 540 - 541
(2007/10/03)
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- Direct thioesterification from carboxylic acids and thiols catalyzed by a Bronsted acid
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In the presence of a catalytic amount of trifluoromethanesulfonic acid, free carboxylic acids reacted with free thiols directly to afford the corresponding thioesters in high yields.
- Iimura, Shinya,Manabe, Kei,Kobayashi, Shu
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- Cleavage of S-S bond by Sm/cat. CoCl2 or Sm/cat. CoCl2 · 6H2O system. A novel method for the synthesis of thiolesters
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The Sm/cat. CoCl2 or Sm/cat. CoCl2 · 6H2O system promoted dlsulfides to react with anhydrides or acyl chlorides to afford thiolesters in good yields under mild and neutral conditions.
- Chen, Rener,Zhang, Yongmin
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p. 3699 - 3704
(2007/10/03)
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- Reductive cleavage of S-S bond in diphenyl disulfide by samarium diiodide: A novel method for the synthesis of thiolesters
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Diphenyl disulfide is reduced by samarium diiodide to yield samarium phenylthiolate. This new thiolate anion species mildly reacts with acyl chlorides to give thiolesters in good yields.
- Jia,Zhang,Zhou
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p. 387 - 392
(2007/10/02)
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