205108-06-1Relevant academic research and scientific papers
Ruthenium-Catalyzed Cross-Metathesis of Allyl Acetate and Styrenes: A Practical Approach to the Synthesis of Tripolinolate A and Its Analogs
Araki, Yasuhiro,Topolov?an, Nikola,Kotora, Martin
, p. 1736 - 1739 (2017)
The scope of the Ru-catalyzed cross-metathesis of allyl acetates and styrenes was explored. A variety of electronically and structurally divergent styrenes were tolerated, and the resultant products were obtained in reasonable yields. The reported method was utilized in the synthesis of inhibitors of the proliferation of glioma and colorectal cancer cells, tripolinolate A and its diacetate analog.
C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles
Patra, Debabrata,Panja, Subir,Saha, Amit
, p. 878 - 883 (2020/02/13)
Starch coated magnetic nanoparticles supported palladium catalyst has been explored to perform C–C cross coupling reactions, such as oxidative Heck coupling and Tsuji–Trost allylic coupling using organosilicon compounds as one of the coupling partners. The biopolymer coated magnetic catalyst was very easy to recover magnetically and was efficiently recycled in the subsequent batches. All the reactions were performed in air and thus the necessity of air and moisture free reaction condition is avoided. The present protocols show wide substrate scope and good yields of the products.
Metal-free, regio- and stereoselective synthesis of linear (E)-allylic compounds using C, N, O, and S nucleophiles
Huang, Xiaojun,Fulton, Brandon,White, Kana,Bugarin, Alejandro
supporting information, p. 2594 - 2597 (2015/06/16)
A variety of allylic acetates and derivatives were synthesized by an efficient two-step protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)- isomer as the sole adduct. This process tolerates several functional groups including halogen-containing molecules, and it is general for weak oxygen, carbon, nitrogen, and sulfur nucleophiles. Furthermore, adducts were obtained in good to excellent yields.
Selenium-catalyzed C(sp3)-H acyloxylation: Application in the expedient synthesis of isobenzofuranones
Kr?tzschmar, Felix,Kassel, Martin,Delony, Daniel,Breder, Alexander
, p. 7030 - 7034 (2015/05/05)
Oxidative Se-catalyzed C(sp3)-H bond acyloxylation has been used to construct a diverse array of isobenzofuranones from simple ortho-allyl benzoic acid derivatives. The synthetic procedure employs mild reaction conditions and gives high chemoselectivity enabled by an inexpensive organodiselane catalyst. The presented approach offers a new synthetic pathway toward the core structures of phthalide natural products.
Pd-catalyzed olefination of perfluoroarenes with allyl esters
Li, Zejiang,Zhang, Yuexia,Liu, Zhong-Quan
supporting information; experimental part, p. 74 - 77 (2012/02/14)
An efficient Pd(II)-catalyzed direct olefination of perfluoroarenes with allyl esters is demonstrated. Under the typical conditions, the coupling reaction of fluorinated-arenes with allylic esters proceeded via a β-H elimination rather than a β-OAc elimin
Palladium-catalyzed selective acyloxylation using sodium perborate as oxidant
Pilarski, Lukasz T.,Janson, Paer G.,Szabo, Kalman J.
supporting information; experimental part, p. 1503 - 1506 (2011/04/25)
Sodium perborate (SPB), a principal component of washing powders, was employed as an inexpensive and eco-friendly oxidant in the palladium-catalyzed C-H acyloxylation of alkenes in excellent regio-and stereochemistry. The reactions used anhydrides as acyloxy sources. The method applies to both terminal and internal alkenes, and even benzylic C-H oxidation.(Figure Presented)
Control of chemo-, regio-, and stereoselectivities in ligand-free Pd-catalyzed oxidative heck reactions of arylboronic acids or alkenylboronate with allyl esters
Su, Yijin,Jiao, Ning
supporting information; experimental part, p. 2980 - 2983 (2009/12/05)
A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. β-H elimination is highly chemoselectively controlled, leading to γ-substituted allyl esters, which is contrary to the traditional
Ligand-free Pd-catalyzed highly selective arylation of allylic esters with retention of the traditional leaving group
Pan, Delin,Chen, Anjun,Su, Yijin,Zhou, Wang,Li, Si,Jia, Wei,Xiao, Juan,Liu, Qingjian,Zhang, Liangren,Jiao, Ning
supporting information; experimental part, p. 4729 - 4732 (2009/02/06)
(Chemical Equation Presented) What leaving group? Organic halides and allylic esters undergo efficient Pd-catalyzed Heck reactions under mild conditions in air to form a new C-C bond without elimination of the β-OAc group in the intermediate palladium complex. Instead a highly regioselective β-H elimination takes place to provide substituted derivatives of allylic alcohols (see scheme).
[(NHC)Au1]-catalyzed rearrangement of allylic acetates
Marion, Nicolas,Gealageas, Ronan,Nolan, Steven P.
, p. 2653 - 2656 (2008/02/09)
Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.
