- Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions
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Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.
- Wang, Xiu,Wang, Zhenhua,Liu, Li,Asanuma, Yuya,Nishihara, Yasushi
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- METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for quantitatively producing a group 14 metal lithium compound under a mild condition. SOLUTION: The method for producing a group 14 metal lithium compound represented by formula (4): R4-nMLin comprises reacting a compound represented by formula (1): R4-nMXn and lithium in the presence of a polycyclic aromatic compound represented by formula (2) or formula (3). [In formula (1) and formula (2), R is a hydrocarbon group; M is a metal atom selected from Si, Ge and Sn; X is a halogen atom or R3M- (R and M are the same as mentioned above); and n is 1 or 2] and [R1 is H or a hydrocarbon group; and m is an integer of 0 to 5.] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0067
(2016/10/31)
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- Stannyl-Lithium: A Facile and Efficient Synthesis Facilitating Further Applications
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We have developed a highly efficient, practical, polycyclic aromatic hydrocarbon (PAH)-catalyzed synthesis of stannyl lithium (Sn-Li), in which the tin resource (stannyl chloride or distannyl) is rapidly and quantitatively transformed into Sn-Li reagent at room temperature without formation of any (toxic) byproducts. The resulting Sn-Li reagent can be stored at ambient temperature for months and shows high reactivity toward various substrates, with quantitative atom efficiency.
- Wang, Dong-Yu,Wang, Chao,Uchiyama, Masanobu
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supporting information
p. 10488 - 10491
(2015/09/28)
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- Potassium carbonate-silica: A highly effective stationary phase for the chromatographic removal of organotin impurities
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Organotin impurities in product mixtures can be reduced from stoichiometric levels to ～15 parts per million by column chromatography using 10% w/w anhydrous potassium carbonate-silica as a stationary phase.
- Harrowven, David C.,Curran, Dennis P.,Kostiuk, Sarah L.,Wallis-Guy, Ian L.,Whiting, Sally,Stenning, Kerri J.,Tang, Bencan,Packard, Emma,Nanson, Lana
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p. 6335 - 6337
(2010/10/02)
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- Axial Chirality in 1,4-Disubstituted (ZZ)-1,3-Dienes. Surprisingly Low Energies of Activation for the Enantiomerization in Synthetically Useful Fluxional Molecules
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Trialkylsilyltrialkylstannes (R3Si-SnR'3) add to 1,6-diynes in the presence of Pd(0) and trispentaflurophenylphosphine to give 1,2-dialkylidenecyclopentanes with terminal silicon and tin substituents. The (ZZ)-geometry of these s-cis-1,3-dienes, resulting from the organometallic reaction mechanisms involved, forces the silicon and tin groups to be nonplanar, thus making the molecules axially chiral. There is rapid equilibration between the two helical forms at room-temperature irrespective of the size of the Si and Sn substituents. However, the two forms can be observed by 1H, 13C, and 119Sn NMR spectroscopy at low temperature. The rates of enantiomerization, which depend on the Si and Sn substituents, and the substitution pattern of the cylopentane ring can be studied by dynamic NMR spectroscopy using line shape analysis. The surprisingly low energies of activation (ΔG? = 52-57 kJ mol-1) for even the bulky Si and Sn derivatives may be attributed to a widening of the exo-cyclic bond-angles of the diene carbons.
- Warren, Sandra,Chow, Albert,Fraenkel, Gideon,Rajanbabu
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p. 15402 - 15410
(2007/10/03)
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- Silylstannation of terminal alkynes using a recyclable palladium(0) catalyst immobilised in an ionic liquid
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Silylstannanes can be regioselectively added across terminal alkynes in a quantitative fashion in the presence of a palladium(0) catalyst immobilised in the [bmim]PF6 ionic liquid which can be recycled without loss of activity.
- Hemeon, Ivan,Singer, Robert D.
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p. 1884 - 1885
(2007/10/03)
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- Cleavage of Sn-Sn Bonds in Hexaalkyl(aryl)stannanes under the Action of Yb(II) Derivatives
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Ytterbium(II) derivatives MeYbI, PhYbI, and YbI2 cleave the Sn-Sn bond in distannanes R′3-SnR′3 (R′ = n-Bu, Ph) to give heterobimetallic derivatives R′3SnYbI, which were identified by products of their hydrolysis, exchange with R″3EHlg (R″ = Ph, Me; E = Ge, Si, Sn) and cross coupling with MeI in the presence of NiCl2(Ph3P)2.
- Syutkina,Rybakova,Novgorodova,Petrov
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- Electrochemical Formation of Dimeric Organostannyl Compounds
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Organosilyl stannanes were formed by electroreduction of the corresponding organostannyl chlorides or distannanes with silyl chlorides.The Sn-C bond formation was also confirmed in the reduction of a mixture of stannyl and alkyl chlorides.
- Ishiwata, Toyoaki,Nonaka, Tsutomu,Umezawa, Masanobu
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p. 1631 - 1634
(2007/10/02)
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