22906-18-9Relevant academic research and scientific papers
Stereospecific Nucleophilic Substitution of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Benzyne
Gui, Yang,Tian, Shi-Kai
, p. 1554 - 1557 (2017/04/13)
A one-pot protocol has been developed for sequential benzyne activation and nucleophilic substitution of enantioenriched tertiary benzylic amines. In the presence of 2-(trimethylsilyl)phenyl triflate and CsF, a range of enantioenriched tertiary benzylic amines were substituted by various nucleophiles, delivering structurally diverse benzylic compounds in moderate to excellent yields with excellent retention of enantiopurity. Importantly, this operationally simple protocol permitted formation of various chiral C-S, C-Se, C-C, and C-N bonds with excellent enantiopurity under metal-free conditions.
Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles
Gellert, Beate A.,Kahlcke, Nils,Feurer, Markus,Roth, Stefanie
supporting information; experimental part, p. 12203 - 12209 (2011/11/07)
Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.
Lewis acid-catalyzed reduction of dithioacetals by 1,4-cyclohexadiene
Ikeshita, Kei-ichiro,Kihara, Nobuhiro,Sonoda, Motohiro,Ogawa, Akiya
, p. 3025 - 3028 (2008/02/06)
Dithioacetals were reduced by 1,4-cyclohexadiene in the presence of a catalytic amount of Lewis acid to afford the corresponding sulfides in good yields.
Selective reduction of thioacetal to sulfide by gallium(II) chloride
Ikeshita, Kei-Ichiro,Kihara, Nobuhiro,Ogawa, Akiya
, p. 8773 - 8775 (2007/10/03)
The reaction of dithioacetals with gallium(II) chloride followed by the acid treatment afforded sulfides in good yields.
A Novel Catalyst System, Trimethylsilyl Chloride and Indium(III) Chloride, as an Efficient Catalyst in the Sulfide Synthesis
Mukaiyama, Teruaki,Ohno, Takashi,Nishimura, Takashi,Han, Jeong Sik,Kobayashi, Shu
, p. 2524 - 2527 (2007/10/02)
O-Trimethylsilyl monothioacetals, which are generally difficult to activate under acidic conditions due to their rapid disproportionation, smoothly react with triethylsilane in the presence of a novel catalyst system, trimethylsilyl chloride and indium(III) chloride, to afford the corresponding sulfides in good to high yields.One pot synthesis of sulfides from aldehydes is also attained in high yields by successive treatment of aldehydes with trimethylsilyl alkyl (aryl) sulfides and triethylsilane in the presence of the above catalyst system under extremely mild conditions.
An Effective Activation of O-Trimethylsilyl Monothioacetal under Extremely Mild Conditions Using a Novel Catalyst System, Trimethylsilyl Chloride and Indium(III) Chloride
Mukaiyama, Teruaki,Ohno, Takashi,Nishimura, Takashi,Han, Jeong Sik,Kobayashi, Shu
, p. 2239 - 2242 (2007/10/02)
A novel catalyst system, trimethylsilyl chloride and indium(III) chloride, effectively catalyzes the reaction of O-trimethylsilyl monothioacetals with triethylsilane and silylated carbon nucleophiles, respectively, to afford the corresponding sulfide derivatives in good to high yields.
Hemin-Catalyzed Addition Reactions of Thiophenols to Styrene
Kano, Koji,Takeuchi, Masayuki,Hashimoto, Shizunobu,Yoshida, Zen-ichi
, p. 1381 - 1384 (2007/10/02)
Hemin promotes the Markovnikov-type addition reactions of thiols (origins of the thiols are their disulfide derivatives) to styrene in benzene-ethanol (1:1) containing NaBH4.The plausible reaction mechanism has been discussed.
ENHANCED NUCLEOPHILE SELECTIVITY IN THE PHOTOADDITION TO STYRENE. COMPARISON WITH THE THERMAL ADDITION
Anderson, Steven W.,Yates, Keith
, p. 2412 - 2421 (2007/10/02)
The reactivity-selectivity properties of the sec-phenethyl carbenium ion and its analogues have been examined in binary-aqueous solutions of alcohols (ROH; R = Me, Et, CF3CH2, n-Bu, t-Bu, n-Pr, i-Pr), acetic acid, and in solutions containig external nucleophiles such as thiophenol, ethanethiol, acetate, and benzenesulfinate.Selectivity (S = k(Nuc)/k(H2O) is observed to be a function of the nucleophile, the ring substituent, thermal or photochemical conditions, irradiation time, and medium acidity.In the case of styrene, the photochemically generated (usually 254 nm, 1 h) species exhibits greater selectivity (up to two orders of magnitude) than its thermal counterpart, generated (usually 80 deg C, 2-4 d) in identical media, particularly in aqueous-rich solvent compositions.A rationale for these differences, supported by fluorescence quenching experiments, and the other effects upon selectivity will be discussed.
