TBAF cleavage

A solution of TBAF in THF (leq., 1 m) was added to a solution of the substrate in THF at 0°C. After ca. 15 min, an excess of saturated ammonium chloride solution was added, and the product was isolated as above. 

Using sulphonic acid ion-exchange resins in ether solvent, selective removal of the trimethylsilyl group from oxygen in bistrimethylsilylated terminal alkynols can be achieved. This method is particularly suitable for low-molecular-weight compounds, where water solubility would make efficient extraction from an aqueous layer difficult. 

Substrate variation resulted in reaction times of 3-80 h, with reaction completion being monitored by g.l.c. 

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The enolate, generated by TBAF cleavage of the enoxysilane derived from phenylselanylacetone, was trapped with benzaldehyde [39] (Scheme 33). The antUsyn ratio of diastereoisomers, easily identified by and Se NMR, was dependent on the temperature and the E or Z structure of the substrate. The borane reduction followed by a conventional acetonization led to a protected syn, syn-l,3-diol. 

Photolysis, 350 nm, CH3CN, H2O. The by-product from the reaction is 2-phenyl-benzo[ ]furan. Cleavage with TBAF and PhCH2SH has been demonstrated (70-94% yield). The related 3,5-dimethoxybenzoin analogue is cleaved with a rate constant of >10 sec Photolytic cleavage occurs by heterolytic bond dissociation. ... 

TBAF, DMF/THF, 64-100% yield. Cleavage occurs in the presence of TMSE and benzyl esters and acetates. ... 

Tetrabutylammonium fluoride (TBAF) is usually used in the form of the trihydrate or as a solution in tetrahydrofuran (THF). The pure form is difficult to isolate, owing to decomposition to FFF, tributylamine, and but-l-ene [18, 19] on dehydration. It has been used for a variety of reactions, including as a catalyst for various reactions with silicon compounds [20, 21]. One of its main uses is in the cleavage of silyl ether protecting groups [22]. 

A 11011-addition procedure based on a tandem retroaldol/epoxide-opening/cycli-zation sequence has been utilized for the elaboration of the dihydrofuran ring of the reduced furanochroman subunit of phomactin A. The strategy utilizes the O-TBS-protected 3-epoxy-(3 -hydroxy ketone 201. Cleavage with TBAF starts the retro-... 

Alternatively, RC CSiMe3 cleavage can be achieved easily, avoiding the use of TBAF, by employing phase-transfer catalysis the reaction is complete in 5-10 min, and the conditions are compatible with other nucleophically labiele functional groups such as epoxides. 

Silanes with heterocyclic residues were also found to be reactive (Equation (20)), although the most likely reason is the in situ cleavage of the heterocyclic residue in the presence of hydrated TBAF to form silanols.290-292 Similarly, among various arylgermanes, only those containing 2-furyl groups were reactive in cross-coupling reactions.293... 

While C-C bond formation via metallation and alkyl or aryl halides is well known (COMC (1982) 5.4.2.7.5), the C-C bond formation with TBAF and aldehyde, enones, or enals is new (Figure 9).318 Carboranyl groups can actually be used as protecting groups for aldehydes and ketones due to the facile cleavage of the cage C-C(OH) bond with... 

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