75732-41-1Relevant articles and documents
Tert-Butyldimethylsilyl Amine (TBDMS-NH2): A Mild and Green Reagent for the Protection of Benzyl Alcohols, Phenols, and Carboxylic Acids under Solvent-Free Conditions
Duczynski, Jeremy A.,Fuller, Rebecca,Stewart, Scott G.
, p. 1172 - 1179 (2016/10/13)
Herein, we present the use of the tert-butyldimethylsilyl amine (TBDMS-NH2) as a silylating reagent for phenols, benzyl alcohols, and carboxylic acids. Unlike other silyl protection reactions, this reported process with TBDMS-NH2 does not involve the form
Two new catalysts for the dehydrogenative coupling reaction of carboxylic acids with silanes - Convenient methods for an atom-economical preparation of silyl esters
Liu, Guo-Bin,Zhao, Hong-Yun,Thiemann, Thies
, p. 2717 - 2727 (2008/02/12)
Tris(triphenylphosphine)cuprous chloride [Cu(PPh3)3Cl] has been found to be an efficient catalyst for the dehydrosilylation of carboxylic acids with silanes. In the presence of 4 mol% Cu(PPh3)3Cl, dehydrosilylation reactions in acetonitrile afforded the corresponding silyl esters at 80°C in good yields. It was noted that triphenylphosphine itself also functions as an adequate catalyst for the reaction. Copyright Taylor & Francis Group, LLC.
Triphenylphosphine-catalyzed dehydrogenative coupling reaction of carboxylic acids with silanes - A convenient method for the preparation of silyl esters
Liu, Guo-Bin,Zhao, Hong-Yun,Thiemann, Thies
, p. 807 - 811 (2008/03/27)
Triphenylphosphine has been found to be an efficient catalyst for the dehydrosilylation of carboxylic acids with silanes. In the presence of 4 mol % of triphenylphosphine (PPh3), dehydrosilylation reactions in DMF afforded the corresponding silyl esters at 120 °C in good yield.
Cationic Au(I)- and Pt(II)-catalyzed silylation of alcohols using allylsilanes
Shibata, Takanori,Kanda, Kazumasa,Ueno, Yasunori,Fujiwara, Ryo
, p. 1146 - 1147 (2007/10/03)
The silylation of alcohols using allylsilanes was catalyzed by cationic Au(I) and Pt(II) species, which were prepared in situ from the metal chlorides ([AuCl(PPh3)], PtCl2) and a silver salt. TBS-, TES-, and TIPS-protections of vario
Effective silylation of carboxylic acids under solvent-free conditions with tert-butyldimethylsilyl chloride (TBDMSCL) and triisopropylsilyl chloride (TIPSCL)
Firouzabadi, Habib,Iranpoor, Naser,Shaterian, Hamid Reza
, p. 71 - 81 (2007/10/03)
Varions types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2°, 3° hydroxyl groups are observed.
The investigation of a transsilylation reaction for the preparation of silyl esters: Reactivity correlated with 29Si NMR resonance frequencies
Weinberg, Jennifer M.,Wooley, Karen L.
, p. 235 - 240 (2007/10/03)
The investigation of a transesterification reaction involving silicon exchange (transsilylation) between a silyl ester and a chlorosilane is reported. The reaction studied involves an equilibrium interchange between trimethylsilyl benzoate and several chlorosilanes, as a preparation of various silyl esters and trimethylsilyl chloride as a volatile by-product. An interesting reactivity balance was observed, in which the reaction with some of the chlorosilanes required an initiating catalyst to proceed. A correlation between the 29Si NMR chemical shifts of the chlorosilanes and their respective reactivities was observed. Chlorosilanes having 29Si NMR chemical shifts greater than 31 ppm (referenced to tetramethylsilane standard at 0 ppm) required the use of a nucleophilic catalyst to initiate the reaction. Reaction of trimethylsilyl benzoate occurred without an initiator with chlorosilanes having 29Si NMR chemical shifts of 5 to 19 ppm; for those resonating between 19 and 31 ppm, an initiator accelerated the reaction and gave improved yields of transsilylated product. N,N-Dimethylformamide and sodium iodide were found to be effective and convenient catalysts/initiators for the reaction.
ON THE POSSIBILITY OF DIOXIRANE FORMATION FROM CRIEGEE PEROXIDE ADDUCTS
Saito, Isao,Nagata, Ryu,Matsuura, Teruo
, p. 2687 - 2690 (2007/10/02)
The possibility of dioxirane formation from thermal and cesium fluoride induced decomposition of α-t-butyldimethylsilyloxyalkyl peroxybenzoates has been examined.
PALLADIUM(II)-CATALYZED EPOXIDATION OF OLEFINS WITH α-SILYLOXYALKYL PEROXYBENZOATES
Nagata, Ryu,Matsuura, Teruo,Saito, Isao
, p. 2691 - 2694 (2007/10/02)
A novel oxygen-atom-transfer reaction from α-silyloxyalkyl peroxybenzoate to olefins by palladium(II) catalyst to give epoxides has been described.
SYNTHESIS OF α-SILYLOXYHYDROPEROXIDES FROM THE REACTION OF SILYL ENOL ETHERS AND HYDROGEN PEROXIDE
Saito, Isao,Nagata, Ryu,Yuba, Kazuaki,Matsuura, Teruo
, p. 1737 - 1740 (2007/10/02)
t-Butyldimethylsilyl enol ethers derived from a wide range of ketones react with hydrogen peroxide in the presence of acid to give remarkably stable α-silyloxyhydroperoxides.
