67124-67-8Relevant academic research and scientific papers
Boron Compounds; 69. Introduction and Removal of t-Butyldimethylsilyl Groups via Diethylboryloxy Compounds
Dahlhoff, Wilhelm V.,Taba, Kalulu M.
, p. 561 - 562 (1986)
O-Diethylboryl compounds react with t-butyldimethylsilylacetylacetonate in the presence of trimethylsilyl triflate at room temperature to give the corresponding t-butyldimethylsilyl ethers, which are easily deprotected, forming O-diethylboryl ethers on re
Rapid assessment of protecting-group stability by using a robustness screen
Collins, Karl D.,Ruehling, Andreas,Lied, Fabian,Glorius, Frank
supporting information, p. 3800 - 3805 (2014/04/03)
An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions. Assessment of up to twelve protecting groups in a single experiment has been demonstrated. Evaluation of this protocol in two unrelated synthetic transformations suggests that this method can be used to select appropriate protecting groups in the design of synthetic routes.
Preparation of nano silica supported sodium hydrogen sulfate: As an efficient catalyst for the trimethyl, triethyl and t-butyldimethyl silylations of aliphatic and aromatic alcohols in solution and under solvent-free conditions
Abri, Abdolreza,Ranjdar, Somayeh
, p. 929 - 934 (2014/10/16)
Nano silica supported sodium hydrogen sulfate has been prepared by mixing NaHSO4 with activated Nano silicagel. We wish to report a new method for the synthesis of trimethyl (TMS), triethyl (TES) and t-butyldimethyl silyl (TBS) ethers from benzylic, allylic, propargylic alcohols, phenols, naphtholes and some of phenolic drugs in the solution and under solvent-free conditions.
Cobalt-mediated diastereoselective cross-coupling reactions between cyclic halohydrins and arylmagnesium reagents
Hammann, Jeffrey M.,Steib, Andreas K.,Knochel, Paul
supporting information, p. 6500 - 6503 (2015/01/09)
Cyclic TBS-protected iodohydrins (and bromohydrins) undergo a highly diastereoselective cross-coupling with various aryl- and heteroarylmagnesium reagents in the presence of THF-soluble CoCl2·2LiCl and TMEDA as a ligand leading to trans-2-arylcyclohexanol derivatives in good yields and dr up to >99:1. A range of functional groups are tolerated in the Grignard reagent (e.g., COOR, CN, CF3, SF5). The use of heterocyclic iodohydrins leads to trans-3,4-disubstituted pyrrolidines and tetrahydrofurans.
Novel electrochemical deoxygenation reaction using diphenylphosphinates
Lam, Kevin,Marko, Istvan E.
, p. 406 - 409 (2011/04/18)
The electrochemical reduction of diphenylphosphinate esters leads smoothly and in high yields to the corresponding deoxygenated products. In comparison with the previously developed methodologies, the electrolysis could be performed at lower temperature and with a higher current density, resulting in a shorter reaction time.
Highly diastereoselective iron-mediated C(sp2)-C(sp3) cross-coupling reactions between aryl grignard reagents and cyclic iodohydrine derivatives
Steib, Andreas K.,Thaler, Tobias,Komeyama, Kimihiro,Mayer, Peter,Knochel, Paul
scheme or table, p. 3303 - 3307 (2011/05/12)
trans-2-Arylcycloalcohol derivatives are obtained in high diastereoselectivity by the iron-mediated cross-coupling of cyclic TBS-protected iodohydrines with aryl Grignard reagents (see scheme; TBS=tert- butyldimethylsilyl). The stereoconvergent cross-coupling of a chiral TBS-protected 2-iodocyclohexanol provides the 2-arylcyclohexanols with no loss of stereochemical purity, and is a valuable alternative to the enantioselective opening of symmetrical epoxides. Copyright
Organic electrosynthesis using toluates as simple and versatile radical precursors
Lam, Kevin,Marko, Istvan E.
experimental part, p. 95 - 97 (2009/03/11)
The electrolysis of toluate esters leads smoothly to the formation of the radical of the alkyl fragment. This property has been used to develop a new electrochemical deoxygenation reaction. The Royal Society of Chemistry.
Toluates: unexpectedly versatile reagents
Lam, Kevin,Markó, István E.
experimental part, p. 10930 - 10940 (2010/02/28)
The mechanism of the monoelectronic reduction of aromatic esters has been investigated. The unexpected synthetic utility of the toluate moiety in the deoxygenation of alcohols and the allylation of ketones is also reported. Finally, the use of aromatic esters as robust, though easily removable, protecting groups is depicted.
Using toluates as simple and versatile radical precursors
Lam, Kevin,Marko, Istvan E.
scheme or table, p. 2773 - 2776 (2009/05/30)
(Chemical Equation Presented) The viability of the toluate moiety as a radical precursor has been examined by studying deoxygenation and cyclization reactions.
Monocoordinating, compact phosphane immobilized on silica surface: Application to rhodium-catalyzed hydrosilylation of hindered ketones
Hamasaka, Go,Ochida, Atsuko,Hara, Kenji,Sawamura, Masaya
, p. 5381 - 5383 (2008/09/16)
(Chemical Equation Presented) Activity without mobility: A compact trialkylphosphane, chemically immobilized on a silica gel surface (see picture), exhibited unique coordination behavior to form a 1:1 Rh/P complex. The monophosphane-{RhCl(cod)} species on
