934-56-5Relevant academic research and scientific papers
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.
Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes
Lian, Chang,Yue, Guanglu,Zhang, Haonan,Wei, Liyan,Liu, Danyang,Liu, Sichen,Fang, Huayi,Qiu, Di
supporting information, p. 4019 - 4023 (2018/10/04)
A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis.
Synthesis of aryl trimethylstannanes from aryl halides: An efficient photochemical method
Chen, Kai,He, Pei,Zhang, Shuai,Li, Pengfei
supporting information, 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.
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
Synthesis of aryl trimethylstannanes from aryl amines: A sandmeyer-type stannylation reaction
Qiu, Di,Meng, He,Jin, Liang,Wang, Shuai,Tang, Shengbo,Wang, Xi,Mo, Fanyang,Zhang, Yan,Wang, Jianbo
supporting information, p. 11581 - 11584 (2013/11/06)
Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright
N-H and N=C bond formation via germanium(III) diradicaloid intermediates and C-S bond cleavage in reactions of the digermyne Ar'GeGeAr' (Ar' = C 6H3-2,6-(C6H3-2,6-Pr i2)2) with a
Wang, Xinping,Ni, Chengbao,Zhu, Zhongliang,Fettinger, James C.,Power, Philip P.
, p. 2464 - 2470 (2009/08/08)
Reactions of the digermyne Ar'GeGeAr' (Ar' = C6H3-2,6(C 6H3-2,6-Pr'2)2) (1) with four different azides R'N3 (R = Me3Sn, nBu3Sn, PhSCH 2, or 1-adamantanyl) a
Phenylboration of monoalkyn-1-yltin compounds
Wrackmeyer, Bernd,Tok, Oleg L.,Milius, Wolfgang
, p. 1509 - 1513 (2008/10/09)
The 1: 1 reactions of triphenylborane 1 with monoalkyn-1-yltin compounds Me3Sn-C≡C-R1 2 [R1 = 1Bu (a), Ph (b), ferrocenyl (c), Si(H)Me2 (d), SnMe3 (e)] afford mainly (> 80%) the corresponding alkene derivatives 3 by 1,1-phenylboration. Exchange B-Ph/Sn-C≡C-R1 takes place as a side reaction. The corresponding 1: 2 reaction with 2b leads to the dialkenylborane 4b (R 1 = Ph), of which the molecular structure could be determined by X-ray analysis. In contrast, the 1:2 reaction with 2e gave an aliene derivative 5e. The solution-state structures of compounds 3-5 have been confirmed by 1H, 11B, 13C and 119Sn NMR spectroscopy.
Metal cation-methyl interactions in CB11Me12 - salts of Me3Ge+, Me3Sn +, and Me3Pb+
Zharov, Ilya,Weng, Tsu-Chien,Orendt, Anita M.,Barich, Dewey H.,Penner-Hahn, James,Grant, David M.,Havlas, Zdenek,Michl, Josef
, p. 12033 - 12046 (2007/10/03)
Oxidation of Me6M2 (M = Ge, Sn) and Me4Pb with the CB11Me12 radical in alkane solvents produced the insoluble salts Me3M+CB11 Me12, - characterized by CP-MAS NMR and EXAFS. The cations interact with methyl groups of CB11Me12- with coordination strength increasing from Pb to Ge. Density functional theory (DFT) calculations for the isolated ion pairs, Me3M+CB11Me 12- (M = Ge, Sn), revealed three isomers with the cation above methyl 2, 7, or 12, and not above a BB edge or a BBB triangle. The interaction has a considerable covalent component, with the cation attempting to perform a backside SE2 substitution on the methyl carbon. In a fourth less favorable isomer the cation is near methyl 1, inclined toward methyl 2, and interacts with hydrogens. DFT atomic charge distributions and plots of the electrostatic potential on the surface of spheres centered at the CB 11H12 and CB11Me12-, icosahedra display the effects of uneven charge distribution within the anion and contradict the common belief that the negative charge of the cage anion is concentrated primarily on the cage boron atoms 7-12; in CB11Me 12-, roughly half is on the cage carbon and the rest on methyls 7-12.
