17113-78-9Relevant academic research and scientific papers
Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones
Lian, Chang,Yue, Guanglu,Mao, Jinshan,Liu, Danyang,Ding, Yi,Liu, Zerong,Qiu, Di,Zhao, Xia,Lu, Kui,Fagnoni, Maurizio,Protti, Stefano
supporting information, p. 5187 - 5191 (2019/07/03)
The visible-light-driven preparation of (hetero)aryl stannanes was carried out under both photocatalyst- and metal-free conditions via irradiation of arylazo sulfones in the presence of hexaalkyldistannanes. The reaction shows a high efficiency and a wide substrates scope. The resulting crude organotin derivatives can be directly employed in a Stille protocol.
A practical method for the preparation of 18F-labeled aromatic amino acids from nucleophilic [18F]fluoride and stannyl precursors for electrophilic radiohalogenation
Zarrad, Fadi,Zlatopolskiy, Boris D.,Krapf, Philipp,Zischler, Johannes,Neumaier, Bernd
, (2018/01/17)
In a recent contribution of Scott et al., the substrate scope of Cu-mediated nucleophilic radiofluorination with [18F]KF for the preparation of 18F-labeled arenes was extended to aryland vinylstannanes. Based on these findings, the potential of this reaction for the production of clinically relevant positron emission tomography (PET) tracers was investigated. To this end, Cu-mediated radiofluorodestannylation using trimethyl(phenyl)tin as a model substrate was re-evaluated with respect to different reaction parameters. The resulting labeling protocol was applied for 18F-fluorination of different electron-rich, -neutral and -poor arylstannyl substrates in RCCs of 16-88%. Furthermore, this method was utilized for the synthesis of 18F-labeled aromatic amino acids from additionally N-Boc protected commercially available stannyl precursors routinely applied for electrophilic radiohalogenation. Finally, an automated synthesis of 6-[18F]fluoro-L-m-tyrosine (6-[18F]FMT), 2-[18F]fluoro-L-tyrosine (2-[18F]F-Tyr), 6-[18F]fluoro-L-3, 4-dihydroxyphenylalanine (6-[18F]FDOPA) and 3-O-methyl-6-[18F]FDOPA ([18F]OMFD) was established furnishing these PET probes in isolated radiochemical yields (RCYs) of 32-54% on a preparative scale. Remarkably, the automated radiosynthesis of 6-[18F]FDOPA afforded an exceptionally high RCY of 54 5% (n = 5).
1,2,3,4-TETRAHYDRO-QUINOLINE DERIVATIVES AS CETP INHIBITORS
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Page/Page column 54; 56, (2008/06/13)
The invention is directed to compounds of Formula (I) described herein useful as CETP inhibitors, compositions containing them, and methods of using them.
Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
Chopa, Alicia B.,Silbestri, Gustavo F.,Lockhart, María T.
, p. 3865 - 3877 (2007/10/03)
A series of arylstannanes have been synthesized, through an SRN1 mechanism, in good to excellent yields (74%-99%) by the photostimulated reaction of trimethyl stannyl ion with substrates supporting different nucleofugal groups. The arylstannanes thus obtained were suitable intermediates for Stille cross-coupling reactions leading to asymmetric bi- and triaryl compounds in acceptable global yields. An attractive feature of this route is that simple commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates, leading the latter to higher global yields of products in fewer steps. The strategies proposed open a broad synthetic tool.
Synthesis of Aromatic and Olefinic Sodium Sulfonates by Electrophilic Destannylation with Trimethylsilyl Chlorosulfonate
Niestroj, Michael,Lube, Andreas,Neumann, Wilhelm P.
, p. 575 - 580 (2007/10/02)
A mild and effective method for the preparation of a variety of aromatic, olefinic, and acetylenic sodium sulfonates is described.The reaction of trialkylaryl- (2a-k) and -heteroarylstannanes (4a-d), bis-(1-alkenyl)dibutylstannanes (6a-f), or trialkylakynylstannanes with trimethylsilyl chlorosulfonate (1) followed by hydrolysis with aqueous NaHCO3 provides the sodium sulfonates in an ipso-specific and in the case of vinylic stannanes stereospecific manner.A comparision of the reactivity of stannylated and silylated olefinic compounds 13 and 14 underlines the greater leaving ability of the stannyl moiety.The in situ preparation of the stannanes makes it possible to apply the synthetic method to natural products such as N-substituted apocodeine (17). - Key Words: Electrophilic aromatic substitution/ Electrophilic vinylic substitution/ Trialkylstannanes, application of/ Arylsulfonates, sodium salts of/ Vinylsulfonates, sodium salts of
DIRECT STANNYLATION OF AROMATIC DERIVATIVES USING BIS(TRIMETHYLSTANNYL) SULPHIDE AND SODIUM
Capozzi, Giuseppe,Menichetti, Stefano,Ricci, Alfredo,Taddei, Maurizio
, p. 721 - 722 (2007/10/02)
The reaction of bis(trimethylstannyl) sulphide and sodium with toluene, m-xylene, p-xylene and thioanisole gives stannylation at the methyl group whereas anisole was stannylated at the aromatic nucleus with very high ortho selectivity
