3769-94-6Relevant academic research and scientific papers
Rh-Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones
Zhang, Kezhuo,Huang, Jiaxin,Zhao, Wanxiang
supporting information, (2022/02/21)
We present herein a novel strategy for the preparation of ketones from aldehydes and allylic boronic esters. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. The key to this successful development is the protodeboronation of alkenyl borylether intermediate via a tetravalent borate anion species in the presence of KHF2 and MeOH. This approach features mild reaction conditions, broad substrate scope, and excellent functional group tolerance. Mechanistic studies also supported that the tandem allylation and chain-walking process were involved.
Generation and reaction of alkyl radicals in open reaction vessels
McErlean, Christopher S. P.,Tatunashvili, Elene
supporting information, p. 7818 - 7821 (2020/11/02)
An operationally simple process to transform alkyl iodides into reactive alkyl radicals is described. Aryl diazonium salts react with Hantzsch esters and molecular oxygen to give aryl radicals, which participate in halogen atom transfers to give alkyl radicals. These intermediates react with a variety of acceptors. The reaction cascade occurs at room temperature, in open reaction vessels, with short reaction times. This journal is
Process for preparing encapsulated metalloporphyrin catalyst and process for oxidation of alcohols
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Page/Page column 4, (2008/06/13)
The present invention relates to a polystyrene encapsulated catalyst containing metalloporphyrin of formula I: wherein R1, R2, and R3 are individually selected from the group consisting of alkyl, halo, nitro and amino groups and M is a metal atom selected from the group consisting of Fe, Co, Ni, Mn, Cu, Ru, Pt and Pd and to its use in oxidation of alcohols.
Thienopyrimidine ureas as novel and potent multitargeted receptor tyrosine kinase inhibitors
Dai, Yujia,Guo, Yan,Frey, Robin R.,Ji, Zhiqin,Curtin, Michael L.,Ahmed, Asma A.,Albert, Daniel H.,Arnold, Lee,Arries, Shannon S.,Barlozzari, Teresa,Bauch, Joy L.,Bouska, Jennifer J.,Bousquet, Peter F.,Cunha, George A.,Glaser, Keith B.,Guo, Jun,Li, Junling,Marcotte, Patrick A.,Marsh, Kennan C.,Moskey, Maria D.,Pease, Lori J.,Stewart, Kent D.,Stoll, Vincent S.,Tapang, Paul,Wishart, Neil,Davidsen, Steven K.,Michaelides, Michael R.
, p. 6066 - 6083 (2007/10/03)
A series of novel thienopyrimidine-based receptor tyrosine kinase inhibitors has been discovered. Investigation of structure-activity relationships at the 5- and 6-positions of the thienopyrimidine nucleus led to a series of N,N′-diaryl ureas that potentl
Solvolysis of caryophyllen-8β-yl derivatives: Biomimetic rearrangement- cyclization to 12-nor-8α-presilphiperfolan-9β-ol
Shankar, Sriram,Coates, Robert M.
, p. 9177 - 9182 (2007/10/03)
The solvolyses of caryophyllen-8β-yl p-nitrobenzoate (14-OpNB) and 15- norcaryophyllen-8β-yl tosylate (15-OTs) were investigated as potential model reactions for the biogenesis of the tricyclic presilphiperfolanol sesquiterpenes. Buffered solvolysis of 14-OpNB in 60% aqueous acetone at 125 °C afforded caryophyllene (3) as major product, accompanied by small amounts of caryophyllen-8β-ol (14-OH) and 5,8-cyclocaryophyllen-4α-ol (16). In contrast, 15-OTs underwent a stereospecific rearrangement-cyclization to 12- nor-8α-presilphiperfolan-9β-ol (17) upon solvolysis in 60% aqueous acetone at 75 °C. The structure and stereochemistry of this trans,cis,trans- tricyclo[6.2.1.05,11]-undecane derivative were established by NMR correlation spectroscopy and X-ray crystallography. Two different mechanisms (paths A and B) for the conversion of 15-OTs to 17 by initial 1,2-migration of either the external or internal cyclobutane ring bonds (C10 and C1) followed by π-σ cyclization onto the trans double bond are discussed.
Palladium-catalyzed acyldemetallation and carbonylation reactions of organomercurials for the synthesis of unsymmetrical ketones
Bumagin, N. A.,More, P. G.,Beletskaya, I. P.
, p. 379 - 388 (2007/10/02)
The palladium-catalyzed acyldemetallation reactions of organomercurials (R2Hg or AlkHgI) provide a mild, selective and general method for the synthesis of unsymmetrical heterocyclic ketones.High yields of ketones (RCOR') were obtained along with small amounts of homocoupling products (R2).The reaction is accelerated by a nucleophilic catalyst with both organic groups of R2Hg taking part in the reaction.The selectivity of the reaction towards the ketone can be increased by carrying out the reaction with a suitable combination of reactants under vacuum.The palladium-catalyzed carbonylation of organomercurials in the presence of ArI is another route to unsymmetrical ketones.The AlkHgI-ArI system undergoes carbonylation in the presence of palladium complex and excess iodide ion under mild conditions to give high yields of unsymmetrical ketones.The selectivity and rate of the reaction depend upon the nature of the catalyst, solvent and the concentration of iodide ion.
Enamines: Part IV - Synthesis of Nitro Substituted Alkyl Phenyl Ketones
Kulkarni, Sheshgiri N.,Bhamare, N. K.,Kamath, H. V.
, p. 168 - 170 (2007/10/02)
Nitro substituted alkyl phenyl ketones (V) have been synthesised by reacting nitro substituted benzoyl chlorides (II) with morpholine enamines (I) of aliphatic aldehydes.The resulting acylated enamines (III) on hydrolysis afford the desired V.However, 2-n
REACTIONS OF ORGANOMETALLIC COMPOUNDS CATALYZED BY TRANSITION METAL COMPLEXES. XIV. SELECTION OF REAGENTS IN THE REACTIONS OF ORGANOMETALLIC COMPOUNDS WITH ORGANIC HALIDES CATALYZED BY PALLADIUM COMPLEXES
Bumagin, N. A.,Ponomarev, A. B.,Beletskaya, I. P.
, p. 1222 - 1231 (2007/10/02)
The effect of the nature of the organic groups in organometallic compounds RM and organic halides R'X (R,R' = Ph, p-MeOC6H4, PhCC, C3H7, Allyl; X = Br, I) on the selectivity and duration of the cross-coupling reactions in the presence of palladium complexes was studied.It was shown that the yield of the cross-coupling product depends not only on the nature of R and R' but also on which of the organic groups is in the organometallic compund and which is in the organic halide.The paths leading to the formation of the homocoupling products in the reactions of organometallic compounds with organic halides through entry of the Pd(0) complex at the C-M bond in the organometallic compound and also as a result of exchange of the organic groups between the R'PdXL2 and RM are discussed.
PALLADIUM- AND NICKEL-CATALYZED ARYL- AND ACYLDEMETALLATION OF ORGANOMETALLIC COMPOUNDS
Bumagin, N. A.,Ponomaryov, A. B.,Beletskaya, I. P.
, p. 129 - 132 (2007/10/02)
Various organometallic compounds obtained in situ from Grignard reagents or organolithiums were compared in reactions with aryl and acyl halides in the presence of transition metal complexes.
A Convenient and Efficient Unsymmetrical Ketone Synthesis from Acid Chlorides and Alkyl Iodides Catalyzed by Palladium
Tamaru, Yoshinao,Ochiai, Hirofumi,Sanda, Fumio,Yoshida, Zen-ichi
, p. 5529 - 5532 (2007/10/02)
Unsymmetrical ketones are prepared in good or excellent yields by a palladium catalyzed coupling reaction of acid chlorides and alkyl iodides meditated by Zn-Cu couple.
