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1461-22-9Relevant articles and documents
Highly stereoselective addition to alkoxy or hydroxy ketones using an α-stannyl ester-stannous chloride system in a chelation-controlled manner
Yasuda,Okamoto,Sako,Baba
, p. 157 - 158 (2001)
The reaction of an α-stannyl ester with α-alkoxy or hydroxy ketones in the presence of SnCl2 gave aldol-type products with high selectivity in a chelation-controlled manner.
INVESTIGATION OF THE DIRECT SYNTHESIS OF TETRABUTYLTIN FROM BUTYL CHLORIDE
Nicholson, John W.,Douek, Josephine A.,Collins, John D.
, p. 173 - 183 (1982)
The direct synthesis of tetrabutyltin from butyl chloride, has been investigated, and the various contributing reactions have been identified.A mechanism is proposed for the overall synthesis, which comprises radical-ionic processes for the liberation of metal atoms from the surfaces of the metal powders, followed by formation of bridging intermediates leading to the transfer of butyl groups from zinc to tin, until the synthesis of tetrabutyltin is complete.Although dibutyltin dihalides were shown to be probable intermediates in the process, the known organohalostannate complex Bu4N+ - was not found to be formed under the conditions used.
Preparation and characterization of dimethoxyphosphine
Centofanti
, p. 1131 - 1133 (1973)
Dimelhoxyphosphine, (CH3O)2PH, has been obtained from the reaction of PF2H, CH3OH, and pyridine and from the carefully controlled reduction of (CH3O)2PCl by (C4H9)3SnH
A highly selective synthesis of R2SnX2 (R = alkyl, X = Br, Cl) species directly from tin and alkyl halides
Ugo, R.,Chiesa, A.,Fusi, A.
, p. 25 - 30 (1987)
The reaction : Sn + 2RX -> SnR2X2 (X = Cl, Br) occurs at relatively low temperature (80 - 120 degC) and with selectives as high as 95 - 99percent in the presence of catalytic system fored by a crown ether and potassium iodide.The reaction is favoured by aprotic dipolar solvents such as dimethylformamide; the presence of an alkyl iodide as cocatalyst has a positive effect, the selectivity remaining unchanged.
Use of the extended one-pot (EOP) procedure for the preparation of ethynylated thiophene derivatives and related palladium-ethynylthiophene organometallic oligomers
Altamura, Patrizia,Giardina, Giorgio,Sterzo, Claudio Lo,Russo, Maria Vittoria
, p. 4360 - 4368 (2001)
The palladium-catalyzed coupling (Stille coupling) of 2,5-diiodothiophene (1) with tributyl(ethynyl)tin forms the 2,5-bis(ethynyl)thiophene (3) and tributyltin iodide as side product (step 1). Addition of lithium diisopropylamide (LDA) to this mixture causes deprotonation of the bis-alkyne and its reaction with the tin halide present in the medium to form the 2,5-bis[(tributyltin)ethynyl]thiophene (4) (step 2). To this mixture was subsequently added trans-dichlorobis(tri-n-butylphosphine)palladium (5), and the corresponding trans-bis(tri-n-butylphosphine)-μ-[2,5-bis(ethynyl)thiophene]palladium oligomer (6) was obtained (step 3). Alternatively, the same route can be directed toward the formation of ethynylated thiophene oligomers: after formation of the 2,5-bis[(tributyltin)ethynyl]thiophene (4) (step 2), addition of 2-iodothiophene (8) or 2-iodo-5-(trimethylsilyl)thiophene (10) led to the formation of 2,5-bis(2-thienylethynyl)thiophene (9) (step 3) and [2-trimethylsilyl(ethynyl)thiophene]-2,5-bisethynylthiophene (11) (step 3′), respectively. The latter can be easily desilylated to obtain the [2-(ethynyl)thiophene]-2,5-bisethynylthiophene (13), while treatment of 9 with sec-BuLi/I2 formed the 2,5-[2,2′-(5,5′-diiodo)bisthienyl]bisethynylthiophene (12). Through a sequence of transformations similar to steps 1-3, the oligo(iodo)ethynylthiophene 12 has been connected to the bis(tri-n-butylphosphine)palladium moiety to form the trans-bis(tri-n-butylphosphine)-μ-[2,2′-bis(ethynyl)thiophene]-2,5-bise thynylthiophene]palladium polymer (15). To compare the advantages of the above extended one-pot (EOP) procedures over classical routes, polymers 6 and 15 were also prepared by the copper-catalyzed reaction of trans-dichlorobis(tri-n-butylphosphine)palladium (5) with 2,5-bis(ethynyl)thiophene (3) and [2-(ethynyl)thiophene]-2,5-bisethynylthiophene (13).
Isocyanide insertion across the Pd-C bond of allenyl and propargyl palladium complexes bearing phosphoquinoline as a spectator ligand. Synthesis of a palladium complex bearing a coordinated cyclobutenyl fragment
Scattolin, Thomas,Visentin, Fabiano,Santo, Claudio,Bertolasi, Valerio,Canovese, Luciano
, p. 5210 - 5217 (2017)
We have studied the insertion of p-toluenesulfonylmethyl isocyanide (TosMIC) on selected allenyl and propargyl complexes of palladium bearing diphenylphosphine quinoline as a spectator ligand. The fast process gives different products depending on the tautomer involved in the reaction. Thus, the unsubstituted allenyl species yields an insertion complex with the isocyanide coordinated between the metal and the first allenyl carbon. On the other hand, a mixture of phenyl substituted allenyl and propargyl palladium complexes yields a novel species characterized by a cyclo-butenyl fragment directly coordinated to palladium. The solid state structure of such a complex together with an exhaustive kinetic study of the whole process is reported.
Synthesis of monophosphines directly from white phosphorus
Scott, Daniel J.,Cammarata, Jose,Schimpf, Maximilian,Wolf, Robert
, p. 458 - 464 (2021/04/09)
Monophosphorus compounds are of enormous industrial importance due to the crucial roles they play in applications such as pharmaceuticals, photoinitiators and ligands for catalysis, among many others. White phosphorus (P4) is the key starting material for the preparation of all such chemicals. However, current production depends on indirect and inefficient, multi-step procedures. Here, we report a simple, effective ‘one-pot’ synthesis of a wide range of organic and inorganic monophosphorus species directly from P4. Reduction of P4 using tri-n-butyltin hydride and subsequent treatment with various electrophiles affords compounds that are of key importance for the chemical industry, and it requires only mild conditions and inexpensive, easily handled reagents. Crucially, we also demonstrate facile and efficient recycling and ultimately catalytic use of the tributyltin reagent, thereby avoiding the formation of substantial Sn-containing waste. Accessible, industrially relevant products include the fumigant PH3, the reducing agent hypophosphorous acid and the flame-retardant precursor tetrakis(hydroxymethyl)phosphonium chloride. [Figure not available: see fulltext.]
Organic tin compound cycle application Stille method of synthesis of biphenyl
-
Paragraph 0051; 0055, (2017/05/12)
The invention provides a method for synthesizing diphenyl through Stille reaction recycling with an organotin compound, and relates to a method for preparing diphenyl through a Stille reaction. A purpose of the present invention is to solve the problem of low organotin utilization rate of the existing Stille method for preparing the diphenyl compound. The method comprises: 1, adopting tri-butyltin chloride and bromobenzene as raw materials, and carrying out a reaction under the effect of a Grignard reagent to synthesize tributylphenyltin; 2, carrying out a reaction of a mixed solution of halogenated benzene, tributylphenyltin, cuprous iodide, lithium chloride, palladium(triphenylphosphine)dichloride and cesium fluoride DMF to prepare diphenyl, and collecting the filter residue; 3, dissolving the filter residue with acetone, dissolving the insoluble matter with absolute alcohol, and concentrating to obtain fluorotributyltin; and 4, converting the tin fluoride into the organic tin chloride with saturated ammonium chloride tetrahydrofuran. According to the present invention, the synthesis process conditions are optimized, the highest yield of the diphenyl compound achieves 97%, and the effective separation utilization of the organic tin chloride is achieved.
Reductive dechlorination of BCl3 for efficient ammonia borane regeneration
Tan, Yingbin,Zhang, Lijun,Chen, Xiaowei,Yu, Xuebin
supporting information, p. 753 - 757 (2015/02/19)
This paper reports a complete ammonia borane (AB) regeneration process in which Bu3SnH was utilized as a reductant for the reductive dechlorination of BCl3, and Et2PhN was selected as a 'helper ligand' to generate Et2PhN·BH3, which gives rise to a high yield of AB by a base-exchange reaction at ambient temperature.
Green synthetic approach to 5-substituted-1h-tetrazoles via recycle and reuse of tributyltin chloride
Sampath,Reddy, V. Prabhakar,Chakravarthy, A. Kalyan,Reddy, P. Pratap
, p. 393 - 396 (2013/02/22)
A simple, safe and efficient process for the recycle of tributyltin chloride from tributyltin hydroxide is developed and its reuse in the synthesis of 5-substituted-1H-tetrazoles is successfully demonstrated, which paved a way to reduce the toxic tin waste significantly. Recycling of tributyltin chloride is possible over six cycles without loss of its activity.