57918-91-9Relevant academic research and scientific papers
Polymer-supported organotin reagents in the catalytic Stille reaction
Hernán, Alejandro G.,Guillot, Vincent,Kuvshinov, Alexander,Kilburn, Jeremy D.
, p. 8601 - 8603 (2003)
Polymer-supported dibutyltin chloride and dimethyltin chloride resins were synthesised and used in Maleczka's catalytic Stille reaction.
Aqueous phase semihydrogenation of alkynes over Ni-Fe bimetallic catalysts
Awasthi, Mahendra K.,Barman, Sudipta Roy,Behrens, Silke,Rai, Rohit K.,Singh, Sanjay K.,Singh, Vipin K.
, p. 4968 - 4980 (2020/08/19)
Bimetallic Ni-Fe catalysts (Ni/Fe, 1?:?1, 1?:?3, and 3?:?1) are synthesized and explored for their catalytic activity in semihydrogenation of internal alkynes using H2 gas in water-ethanol solution. Our findings revealed that over the Ni1Fe3 catalyst a high diastereoselectivity for Z-alkenes with a high conversion for a wide range of internal alkynes can be achieved at moderate reaction temperature (40 °C). Notably, the selectivity for the Z-alkenes is enhanced in the presence of n-butyl amine as an additive. Deuterium labeling experiments evidenced that H2 gas becomes dissociated homolytically over the catalyst surface to hydrogenate alkynes to alkenes. Synthesized catalysts were successfully characterized by HR-TEM, SEM, XPS, EDS, P-XRD and H2-TPD.
Copper-Catalyzed Alkenylation of Alcohols with β-Nitrostyrenes via a Radical Addition-Elimination Process
Guo, Sheng-Rong,Yuan, Yan-Qin
supporting information, p. 1961 - 1968 (2015/09/01)
A new method for the preparation of allylic alcohol derivatives has been developed via a radical mechanism using DTBP as the radical initiator promoted by copper salt. The C(sp3)-H bond in various alcohols, toluene derivatives, and alkanes were successfully converted into C-C bonds to yield the desired products in moderate to good yields.
Palladium-catalyzed selective Heck-type diarylation of allylic esters with aryl halides involving a β-OAc elimination process
Liu, Yan,Yao, Bo,Deng, Chen-Liang,Tang, Ri-Yuan,Zhang, Xing-Guo,Li, Jin-Heng
supporting information; experimental part, p. 1126 - 1129 (2011/04/23)
Palladium-catalyzed selective Heck-type diarylation of allylic esters with aryl halides has been developed. Allylic esters are reacted with aryl iodides to provide the corresponding 1,3-diaryl propenes through a β-OAc elimination process. It is noteworthy that the methodology can be applied in constructing the indole and benzofuran skeletons.(Figure Presented)
Reactions of vinyltributylgermanes and aryl halides under Heck conditions
Torres, Nicole M.,Lavis, Jér?me M.,Maleczka Jr., Robert E.
experimental part, p. 4407 - 4410 (2009/10/26)
We describe the palladium-mediated reaction of vinyltributylgermanes with aryl halides under Heck conditions. Depending on their degree of substitution, (E)-vinyltributylgermanes preferentially afford either the cine or Z-alkenyl coupled products in moder
New and efficient synthesis of solid-supported organotin reagents and their use in organic synthesis
Hernán, Alejandro G.,Horton, Peter N.,Hursthouse, Michael B.,Kilburn, Jeremy D.
, p. 1466 - 1475 (2007/10/03)
Novel resin-bound organotin reagents have been prepared, including for the first time resin-bound dimethyl tin reagents. Mild methodology has also been developed for the very efficient synthesis of resin-bound distannanes. The resin-bound tin chloride rea
Stille reactions catalytic in tin: A "Sn-F" route for intermolecular and intramolecular couplings
Gallagher, William P.,Maleczka Jr., Robert E.
, p. 841 - 846 (2007/10/03)
(Chemical Equation Presented) Polymethylhydrosiloxane (PMHS) made hypercoordinate by KF(aq) allows Me3SnH to be recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Starting with a variety of alkynes, in situ vinyltin formation is followed by Stille reaction with aryl, styryl, benzyl, or vinyl electrophiles present in the reaction mixture. Both inter- and intramolecular versions of the process are possible with tin loads of approximately 6 mol %. Regeneration of the organotin hydride is believed to proceed through a Me3SnF intermediate. Given the aggregated nature of organotin fluorides and the ability to use these organotins in substoichiometric quantities, the hazards and purification problems associated with the removal of organotin wastes from reaction mixtures are minimized.
Heck reactions of aryl bromides with alk-1-en-3-ol derivatives catalysed by a tetraphosphine/palladium complex
Berthiol, Florian,Doucet, Henri,Santelli, Maurice
, p. 5633 - 5636 (2007/10/03)
cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Heck reaction of alk-1-en-3-ol with a variety of aryl bromides. In the presence of hex-1-en-3-ol or oct-1-en-3-ol, the β-arylated carbonyl compounds were selectively obtained. Linalool and 2-methylbut-3-en-2-ol led to the corresponding 1-arylalk-1-en-3-ol derivatives. Turnover numbers up to 69,000 can be obtained for this reaction. A minor electronic effect of the substituents of the aryl bromide was observed. Similar reaction rates were observed in the presence of activated aryl bromides such as bromoacetophenone and deactivated aryl bromides such as bromoanisole.
Stille couplings catalytic in tin: a "Sn-F" approach.
Maleczka Jr.,Gallagher
, p. 4173 - 4176 (2007/10/03)
A new tin recycling method for Stille couplings catalytic in tin is reported. PMHS made hypercoordinate by KF((aq)) allows Me(3)SnH to be efficiently recycled during a Pd(0)-catalyzed hydrostannation/Stille cascade. Relative to previously disclosed protoc
STEREOSELECTIVE SYNTHESIS OF 5-ARYL-3-METHYL-2E,4E-PENTADIENALS
Makin, S. M.,Mikerin, I. E.,Dobretsova, E. K.,Shavrygina, O. A.
, p. 572 - 575 (2007/10/02)
A series of 5-aryl-3-methyl-2E,4E-pentadienals were synthesized stereoselectively from 4-aryl-3E-buten-2-ones and methylmagnesium iodide followed by formylation of the obtained tertiary dimethylstyrylcarbinols by the formylating complex produced from dimethylformamide and phosphorus oxychloride.A synthesis of 2,3,6-trimethyl-4-methoxybenzaldehyde, starting from pseudocumene, is proposed.
