18765-67-8Relevant academic research and scientific papers
Metal-Free Ammonium Iodide Catalyzed Oxidative Dehydrocoupling of Silanes with Alcohols
Yuan, Yan-Qin,Kumar, Pailla Santhosh,Guo, Sheng-Rong
supporting information, p. 1620 - 1623 (2017/08/11)
An ammonium iodide catalyzed direct oxidative coupling of silanes with alcohols to give various alkoxysilane derivatives was discovered. tert -Butyl hydroperoxide proved to be an efficient oxidant for this transformation. Attractive features of this protocol include its transition-metal-free nature and the mild reaction conditions.
One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols
Bergueiro, Julian,Montenegro, Javier,Saa, Carlos,Lopez, Susana
, p. 14475 - 14479 (2014/04/17)
Aluminium trichloride catalyses the expeditious direct conversion of tetrahydropyranyl ethers to silyl ethers. This one-step transformation is chemoselective versus deprotection of the acetal and hydrosilylation of unsaturated carbon-carbon bonds, and can also be applied to linear acetals. A possible mechanism is tentatively proposed. This journal is the Partner Organisations 2014.
Unsuccessful attempts to add alcohols to transient 2-amino-2-siloxy- silenes-leading to a new benign route for base-free alcohol protection
Guliashvili, Tamaz,Tibbelin, Julius,Ryu, Jiyeon,Ottosson, Henrik
supporting information; experimental part, p. 9379 - 9385 (2011/01/07)
Thermolytic formation of transient 1,1-bis(trimethylsilyl)-2-dimethylamino- 2-trimethylsiloxysilene (2) from N,N-dimethyl(tris(trimethylsilyl)silyl) methaneamide (1) in presence of a series of alcohols was investigated. The products are, however, not the expected alcohol-silene addition adducts but silylethers formed in nearly quantitative yields. Thermolysis of 1 in the presence of both alcohols (MeOH or iPrOH) and 1,3-dienes (1,3-butadiene or 2,3-dimethyl-1,3-butadiene) gives alkyl-tris(trimethylsilyl)silylethers and the [4+2] cycloadducts between the silene and diene, which confirms the presence of 2 and that it is unreactive towards alcohols. The observed silylethers are substitution adducts where the amide group of the silylamide is replaced by an alkoxy group, and the reaction time is reflected in the steric bulk of the alcohol. Indeed, the formation of silylethers from the reaction of alcohols with silylamide represents a new base-free method for protection of alcohols. The protection reactions using 1 progresses at elevated temperatures, or alternatively, under acid catalysis at ambient temperature, and similar protections can be carried out with N-cyclohexyl(triphenylsilyl)methaneamide and N,N-dimethyl(trimethylsilyl)methaneamide. The latter silylamide can be used under neutral conditions at room temperature. The only by-products are formamides (N,N-dimethylformamide (DMF) or N-cyclohexylformamide), and the reactions can be performed without solvent. In addition to alcohols we also examined the method for protection of diols, thiols and carboxylic acids, and also these reactions proceeded in high yields and with good selectivities. The Royal Society of Chemistry.
