30263-03-7Relevant academic research and scientific papers
Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles
Bandar, Jeffrey S.,Reidl, Tyler W.
supporting information, p. 11939 - 11945 (2021/08/20)
Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional groups. The utility of this method is demonstrated by the synthesis of pharmaceutical analogues and its use in multicomponent reactions.
Generation of γ-oxy-substituted benzylithium derivatives by reductive lithiation of 4-phenyl-1,3-dioxanes
Azzena, Ugo,Pilo, Luciano
, p. 664 - 668 (2007/10/03)
Reductive cleavage of 1,3-dioxanes 1a-c with Li metal in the presence of a catalytic amount of naphthalene in THF, followed by reaction with different electrophiles, allowed the synthesis of 3-substituted- and 3,3-disubstituted- 3-phenylpropan-1-ols 4 in good yields.
Microwave-assisted reduction of β-trimethylsilyl carbonyl compounds by sodium borohydride
Zadmard,Saidi,Bolourtchian,Nakhshab
, p. 63 - 66 (2007/10/03)
Several β-trimethylsilyl carbonyl compounds were reduced by sodium borohydride to produce β-trimethylsilylated alcohol under microwave irradiation in short time and good yields.
REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALLYLTRIMETHYLSILANES VIA KRIEF-REICH ELIMINATION IN β-SELENO-γ-SILYL ALCOHOLS
Sarkar, Tarun K.,Ghosh, Sunil K.,Satapathi, Tushar K.
, p. 1885 - 1898 (2007/10/02)
The synthesis of (E)-allyltrimethylsilanes by regio- and stereocontrolled pathways is described based on the preference for Krief-Reich elimination over silicon-controlled rearrangement in β-seleno-γ-silyl alcohols, readily available from α-selenoaldehydes, 10 - 12.Usefulness of this protocol for the introduction of the allylsilane function α to the carbonyl group in cycloalkanones as well as for the preparation of unsymmetrically substituted allylsilanes is also reported.
Carbanion Rearrangements of ω-Phenyl-ω-(trimethylsilyl)alkyllithium Compounds: Intramolecular Reactions of Benzyltrimethylsilanes with a Carbon-Lithium Bond
Maercker, Adalbert,Stoetzel, Reinhard
, p. 1695 - 1706 (2007/10/02)
ω-Phenyl-ω-(trimethylsilyl)alkyllithium compounds show four out of five theoretically conceivable possibilities for intramolecular stabilization depending on the solvent and on the chain length n.While transmetalation of a methyl group at the silicon atom by a 1,(n+2) proton transfer is observed in any case, the intramolecular 1,n shift of the benzylic proton does only take place with n >/= 4.The main reaction, however for n = 3 and 4 only, is represented by the 1,n trimethylsilyl shift via a cyclic ate complex as an intermediate which partly splits off methyllithium yielding the corresponding silacycloalkane derivatives.In going from diethyl ether to THF as the solvent, the silyl shifts are more accelerated than the proton shifts.In no case, however, a Grovenstein-Zimmermann rearrangement involving phenyl migration took place.Degenerate silyl shifts starting from α-deuterated ω-(trimethylsilyl)alkyllithium compounds could not be detected either.Only by introduction of a second trimethylsilyl group into the 3 position a 1,3-(C -> C)-trimethylsilyl shift is initiated again.
