940-00-1Relevant articles and documents
Reductive Electrophotocatalysis: Merging Electricity and Light to Achieve Extreme Reduction Potentials
Kim, Hyunwoo,Kim, Hyungjun,Lambert, Tristan H.,Lin, Song
supporting information, p. 2087 - 2092 (2020/02/04)
We describe a new electrophotocatalytic strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of -3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (Ered ≈ -1.9 to -2.9 V). The resultant aryl radicals can be engaged in various synthetically useful transformations to furnish arylboronate, arylstannane, and biaryl products.
Synthesis of Arylstannanes via Palladium-Catalyzed Decarbonylative Coupling of Aroyl Fluorides
Kayumov, Muzaffar,Zhao, Jian-Nan,Mirzaakhmedov, Sharafitdin,Wang, Dong-Yu,Zhang, Ao
supporting information, p. 776 - 781 (2019/11/14)
Aryl stannanes are valuable precursors in organic transformations, but their synthetic methods are limited. Here we present a Pd-catalyzed decarbonylative stannylation of acid fluorides in the absence of exogenous base. Various aryl stannanes were efficiently prepared from bench-stable transition metal catalyst and ligand with broad functional group compatibility and substrate scope including natural products and pharmaceuticals. This protocol was also successfully used to a late-stage diversification of an existing uricosuric drug probenecid. (Figure presented.).
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.
Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature
Mao, Shuai,Chen, Zhengkai,Wang, Lu,Khadka, Daulat Bikram,Xin, Minhang,Li, Pengfei,Zhang, San-Qi
, p. 463 - 471 (2019/01/10)
BF3·OEt2-mediated cross-coupling of (SnMe3)2 with aryl triazene offers a new strategy for the synthesis of aryl stannane. A variety of synthetically useful aryl trimethylstannanes were produced in moderate to good yields with this metal-free approach. One-pot sequential Stille cross-coupling with different aryl bromides provides a short entry to both symmetrical and unsymmetrical biaryl compounds.
SUBSTITUTED BENZAZINONES AS ANTIBACTERIAL COMPOUNDS
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Page/Page column 253, (2017/07/14)
The present invention relates to LpxC antibacterial compounds of Formula (1A), corresponding pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions:, compound preparation, treatment methods and uses for bacterial infections, especially those caused by gram-negative bacteria.
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).
Synthesis of aryl trimethylstannanes from aryl halides: An efficient photochemical method
Chen, Kai,He, Pei,Zhang, Shuai,Li, Pengfei
, p. 9125 - 9128 (2016/07/21)
An efficient transition-metal-free photochemical method featuring excellent functional group tolerance, mild reaction conditions and short reaction times has been discovered and developed for the synthesis of (hetero)aryl trimethylstannanes from (hetero)aryl halides. A photo-initiated radical chain mechanism was proposed based on preliminary mechanistic studies.
Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF
Makaravage, Katarina J.,Brooks, Allen F.,Mossine, Andrew V.,Sanford, Melanie S.,Scott, Peter J. H.
supporting information, p. 5440 - 5443 (2016/11/04)
A copper-mediated nucleophilic radiofluorination of aryl- and vinylstannanes with [18F]KF is described. This method is fast, uses commercially available reagents, and is compatible with both electron-rich and electron-deficient arene substrates. This method has been applied to the manual synthesis of a variety of clinically relevant radiotracers including protected [18F]F-phenylalanine and [18F]F-DOPA. In addition, an automated synthesis of [18F]MPPF is demonstrated that delivers a clinically validated dose of 200 ± 20 mCi with a high specific activity of 2400 ± 900 Ci/mmol.
1,2-AZABORINE COMPOUNDS AND SYNTHESIS
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Page/Page column 15-16, (2014/02/16)
A compound, or a pharmaceutically acceptable salt or ester thereof, having a structure of formula (I), wherein R1 is a substituted aryl or an optionally-substituted heteroaryl, provided that the heteroaryl is not pyridyl or azaborine; and each
Synthesis of thiophene 1,1-dioxides and tuning their optoelectronic properties
Tsai, Chia-Hua,Chirdon, Danielle N.,Maurer, Andrew B.,Bernhard, Stefan,Noonan, Kevin J. T.
supporting information, p. 5230 - 5233 (2013/11/06)
A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1
