60632-83-9Relevant academic research and scientific papers
Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes
Shirini, Farhad,Khaligh, Nader Ghaffari,Akbari-Dadamahaleh, Somayeh
, p. 15 - 23 (2013/01/14)
Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
Preparation, characterization and use of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an eco-benign, efficient and reusable ionic liquid catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups
Khaligh, Nader Ghaffari
experimental part, p. 63 - 70 (2011/12/02)
New and novel ionic liquid (3-methyl-1-sulfonic acid imidazolium hydrogen sulfate) is a recyclable and eco-benign catalyst for the chemoselective trimethylsilyl protection of hydroxyl groups under solvent-free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-8 min). The catalyst was characterized by FT-IR, 1H NMR and 13C NMR studies. All the products were extensively characterized by 1H NMR, IR, GC-MS and melting point analyses. A mechanism for the catalytic activity is proposed. The catalyst can be recovered and reused without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.
Succinimide-N-sulfonic acid: A mild, efficient, and reusable catalyst for the chemoselective trimethylsilylation of alcohols and phenols
Shirini,Khaligh, Nader Ghaffari
experimental part, p. 2156 - 2165 (2012/04/10)
Succinimide-N-sulfonic acid (SuSA) is easily prepared by the reaction of succinimide with chlorosulfonic acid. This reagent is able to efficiently catalyze the chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). All reactions were performed under mild reaction conditions, giving excellent yields. Copyright Taylor & Francis Group, LLC.
[SnIV(TPP)(BF4)2]: An efficient and reusable catalyst for chemoselective trimethylsilylation of alcohols and phenols with hexamethyldisilazane
Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Gharaati, Shadab
experimental part, p. 212 - 219 (2010/04/04)
Tin(IV)tetraphenylporphyrinato tetrafluoroborate, [SnIV(TPP)(BF4)2], was used as an efficient catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane (HMDS). High-valent [SnIV(TPP)(BF4)2] catalyzes trimethylsilylation of primary, secondary and tertiary alcohols as well as phenols, and the corresponding TMS-ethers were obtained in high yields and short reaction times at room temperature. While, under the same reaction conditions [SnIV(TPP)Cl2] is less efficient to catalyze these reactions. One important feature of this catalyst is its ability in the chemoselective silylation of primary alcohols in the presence of secondary and tertiary alcohols and phenols. The catalyst was reused several times without loss of its catalytic activity.
Nafion SAC-13: heterogeneous and reusable catalyst for the activation of HMDS for efficient and selective O-silylation reactions under solvent-free condition
Rajagopal, Gurusamy,Lee, Hanbin,Kim, Sung Soo
experimental part, p. 4735 - 4741 (2009/10/09)
Nafion SAC-13 effectively activates hexamethyldisilazane (HMDS) for the efficient and selective silylation of alcohols. Primary, secondary, and tertiary alcohols and phenols are efficiently converted to their corresponding silylethers in short reaction ti
Mild and efficient silylation of alcohols and phenols with HMDS using Bi(OTf)3 under solvent-free condition
Kadam, Santosh T.,Kim, Sung Soo
experimental part, p. 2562 - 2566 (2009/12/24)
A very efficient and mild silylation of alcohols and phenols with hexamethyldisilazane (HMDS) at rt is developed using Bi(OTf)3 as the catalyst. Primary, secondary and tertiary alcohols as well as phenols are excellently converted into correspo
Asymmetrie allylation of methyl ketones by using chiral phenyl carbinols
Tietze, Lutz F.,Kinzel, Tom,Wolfram, Thomas
experimental part, p. 6199 - 6210 (2010/03/01)
Novel chiral auxiliaries for the stereoselective allylation of aliphatic methyl ketones with allyltrimethylsilane and their use in the synthesis of homoallylic ethers are described. In a multicomponent domino process catalyzed by trifluoromethanesulfonic
