63522-99-6Relevant academic research and scientific papers
Mechanistic studies on the SCS-pincer palladium(II)-catalyzed tandem stannylation/electrophilic allylic substitution of allyl chlorides with hexamethylditin and benzaldehydes
Pijnenburg, Niels J. M.,Cabon, Yves H. M.,Van Koten, Gerard,Klein Gebbink, Robertus J. M.
, p. 4858 - 4868 (2013/05/23)
This paper describes a mechanistic study of the SCS-pincer Pd II-catalyzed auto-tandem reaction consisting of the stannylation of cinnamyl chloride with hexamethylditin, followed by an electrophilic allylic substitution of the primary tandem-reaction product with 4-nitrobenzaldehyde to yield homoallylic alcohols as the secondary tandem products. As it turned out, the anticipated stannylation product, cinnamyl trimethylstannane, is not a substrate for the second part of the tandem reaction. These studies have provided insight in the catalytic behavior of SCS-pincer PdII complexes in the auto-tandem reaction and on the formation and possible involvement of Pd0 species during prolonged reaction times. This has led to optimized reaction conditions in which the overall tandem reaction proceeds through SCS-pincer PdII-mediated catalysis, that is, true auto-tandem catalysis. Accordingly, this study has provided the appropriate reaction conditions that allow the pincer catalysts to be recycled and reused. Minor isomer, major importance: A mechanistic study of the SCS-pincer Pd-catalyzed auto-tandem reaction is described consisting of the stannylation of cinnamyl chloride, followed by an electrophilic allylic substitution of the primary tandem reaction product to yield homoallylic alcohols (see scheme; SCS=[2,6-(CH2SPh)2C6H3] -). This study pointed out that the anticipated stannylation product, cinnamyl trimethylstannane, is not a substrate for the second part of the tandem reaction. Copyright
UROKINASE INHIBITORS
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, (2008/06/13)
Disclosed are benzothiophene and thienothiophene derivatives useful for inhibiting urokinase activity.
Free radical and palladium-catalysed hydrostannation of allenes: a comparison
Mitchell, Terence N.,Schneider, Ulrich
, p. 195 - 199 (2007/10/02)
While free radical hydrostannation of monosubstituted allenes with Me3SnH affords mixtures of varying composition, cyclohexylidene allene is attacked by the stannyl radical preferentially at the central carbon atom.In contrast, palladium-catalysed hydrostannation involves a regioselective attachment of the organotin moiety to the less highly substituted terminal carbon atom of the allene framework.
