14506-32-2Relevant academic research and scientific papers
Scandium trifluoromethanesulfonate, a novel catalyst for the addition of allyltrimethylsilane to aldehydes
Aggarwal, Varinder K.,Vennall, Graham P.
, p. 3745 - 3746 (1996)
Scandium triflate (2-10 mol%) has been found to be a highly efficient catalyst for the addition of allyltrimethylsilane to both aromatic and aliphatic aldehydes.
Tin mediated Barbier type allylation in ionic liquids
Slaton, Rahiem,Petrone, Adam,Manchanayakage, Renuka
, p. 5073 - 5076 (2011)
The Barbier type allylation of carbonyl compounds is a useful organic transformation as the resultant homoallylic alcohols are important building blocks for many biologically active molecules. Tin mediated Barbier allylation of different carbonyl compounds in room temperature ionic liquid, [BMIM][BF 4] afforded the corresponding homoallylic alcohols in good to excellent yields. The ionic liquid was successfully recycled and reused in allylation reactions.
Carbonyl allylation of aldehydes catalyzed by a silica-supported poly-γ-diphenylarsinopropylsiloxane palladium(0) complex
Cai, Mingzhong,Huang, Yizheng,Zhao, Hong,Zhang, Rongli
, p. 2436 - 2440 (2004)
A silica-supported poly-γ-diphenylarsinopropylsiloxane palladium (0) complex has been prepared from γ-chloropropyltriethoxysilane via immobilization on fumed silica, followed by reacting with potassium diphenylarsenide and palladium chloride, and then the reduction with hydrazine hydrate. The palladium(0) complex has been found to catalyze the allylation of aldehydes via the formation of π-allylpalladium complexes, using allylic chlorides as allylating agent and SnCl2 as reducing agent. This polymeric palladium complex can be recovered and reused.
1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C–H Acid for Br?nsted and Lewis Acid Catalysis
H?fler, Denis,van Gemmeren, Manuel,Wedemann, Petra,Kaupmees, Karl,Leito, Ivo,Leutzsch, Markus,Lingnau, Julia B.,List, Benjamin
, p. 1411 - 1415 (2017)
Tetratrifylpropene (TTP) has been developed as a highly acidic, allylic C–H acid for Br?nsted and Lewis acid catalysis. It can readily be obtained in two steps and consistently shows exceptional catalytic activities for Mukaiyama aldol, Hosomi–Sakurai, an
Weaker lewis acid, better catalytic activity: Dual mechanisms in perfluoroarylborane-catalyzed allylstannation reactions
Morrison, Darryl J.,Piers, Warren E.
, p. 2857 - 2860 (2003)
(Matrix is presented) PhB(C6F5)2 exhibits much higher activity as a Lewis acid catalyst for the allylstannation of aromatic aldehydes than the stronger Lewis acid B(C6F 5)3. This anomalous enhancement of catalytic activity for the weaker LA is shown to be partly due to decreased thermodynamic stability of ion pair 2b relative to 2a in the product-forming step of the reaction. A mechanistic path where the borane serves as the true LA catalyst is more important for the weakly Lewis acidic borane.
Allylation of aldehyde and imine substrates with in situ generated allylboronates - A simple route to enatioenriched homoallyl alcohols
Sebelius, Sara,Szabo, Kalman J.
, p. 2539 - 2547 (2005)
Allylation of aldehyde and imine substrates was achieved using easily available allylacetates and diboronate reagents in the presence of catalytic amounts of palladium. This operationally simple one-pot reaction has a broad synthetic scope, as many functionalities including, acetate, carbethoxy, amido and nitro groups are tolerated. The allylation reactions proceed with excellent regio- and stereoselectivity affording the branched allylic isomer. By employment of commercially available chiral diboronates enantioenriched homoallyl alcohols (up to 53 % ee) could be obtained. The mechanistic studies revealed that the in situ generated allylboronates react directly with the aldehyde substrates, however the allylation of the sulfonylimine substrate requires palladium catalysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Allylation reactions of carbonyl compounds using an organosilicon reagent in aqueous media
Aoyama, Naohiro,Hamada, Tomoaki,Manabe, Kei,Kobayashi, Shu
, p. 676 - 677 (2003)
Allylation reactions of carbonyl compounds such as aldehydes and reactive ketones using allyltrimethoxysilane in aqueous media proceeded smoothly in the presence of 5 mol% of a CdF2-terpyridine complex; the presence of the ligand plays an impor
Lewis acid-promoted addition of allyl(cyclopentadienyl)iron(II) dicarbonyl to aldehydes: A new aldehyde allylation method
Agoston, Gregory E.,Cabal, Maria P.,Turos, Edward
, p. 3001 - 3004 (1991)
The Lewis acid-promoted addition of allyliron(II) reagent 4 to aldehydes provides zwitterionic iron-olefin complexes 7 as isolable yellow salts. Treatment of the iron complexes with NaI in wet acetone affords homoallylic alcohols 8.
Simple Modular Synthetic Approaches to Asymmetric NN'N'', NN' C, or NN' P -Type Amido Pincer Ligands: Synthesis, Characterisation, and Preliminary Ligation Studies
Herasymchuk, Khrystyna,Huynh, Jennifer,Lough, Alan J.,Roces Fernández, Laura,Gossage, Robert A.
, p. 2121 - 2129 (2016)
A simple modular approach is presented which has been directed towards the synthesis of potentially monoanionic NN'N'', NN'C, and NN'P pincer-type ligands. These pincers incorporate an amide functionality derived from the skeletal structure of readily available 2-(2-aminophenyl)-4,5-dioxooxazoles. All of the pincers are synthesized in moderate yields (up to 74%) and are characterised by nuclear magnetic spectroscopy (NMR), elemental analyses, and infrared (IR) spectroscopy. X-ray crystallography is also performed on the chiral and achiral alkyl halide precursors and on an oxide derivative of a pincer with a NN'P-atom donor set. A palladium derivative of one of the NN'N''-pincers is shown to be an active catalyst for the addition of an allyl group to various benzaldehydes using n-Bu3Sn(allyl) as allyl source.
Unusual Carbonyl Differentiation in the Lewis Acid-Catalyzed Allylation of Aldehydes with Tetraallyltin. Applications to Parallel Recognition and Shotgun Process
Nagano, Yoshifumi,Orita, Akihiro,Otera, Junzo
, p. 2183 - 2189 (2003)
In contrast to conventional substrate selectivity in Lewis-acid promoted nucleophilic reactions wherein less electrophilic aldehydes react preferentially over the more electrophilic counterparts, addition of tetraallyltin to aldehydes occurs in a reversed sense. The substrate selectivity in Lewis acid-promoted nucleophilic addition is generally dependent on the combinations of substrates, nucleophiles, catalysts, etc. Such diversity leads to two one-pot protocols, parallel recognition and shotgun process wherein different chemical transformations take place directly on the separate reaction sites without recourse to protection-deprotection procedures. These two protocols are tunable by controlling the electronic properties of the substrates.
