59875-97-7Relevant academic research and scientific papers
Copper-Catalyzed Cascade Radical Addition-Cyclization Halogen Atom Transfer between Alkynes and Unsaturated α-Halogenocarbonyls
Gao, Yuzhen,Zhang, Pengbo,Ji, Zhe,Tang, Guo,Zhao, Yufen
, p. 186 - 190 (2017)
A Cu-catalyzed cascade radical addition/cyclization/halogen atom transfer between alkynes and α-halogeno-γ, δ-unsaturated carbonyl compounds for the synthesis of various substituted cyclopentenes is described. Since up to four Csp3-Csp2 bonds, two Csp3-Br bonds, and two carbocycles can be established in a single reaction, this 100% atom-efficient reaction exhibits the advantages of wide substrate scope, high functional group tolerance, and step-economics, and it offers an entry of the atom transfer radical addition/cyclization (tandem ATRA-ATRC) process to the synthesis of substituted cyclopentenes.
Synthesis and evaluation of ion-imprinted composite membranes of Cr(vi) based on β-diketone functional monomers
Cheng, Huiling,Hong, Yuwen,Hu, Xianzhi,Li, Peng,Wang, Guifang,Wang, Xin,Zhao, Li,Zi, Futing
, p. 38915 - 38924 (2021/12/20)
Using Cr(vi) as the imprinted ions and 2-allyl-1,3-diphenyl-1,3-propanedione (ADPD) (a compound synthesized by independent design) as the functional monomer, a series of chromium ion-imprinted composite membranes (Cr(vi)-IICMs) and corresponding non-impri
Synthesis of 3-Carbonyl Trisubstituted Furans via Pd-Catalyzed Aerobic Cycloisomerization Reaction: Development and Mechanistic Studies
Barboza, Amanda A.,Neto, Attilio Chiavegatti,Rosset, Isac G.,Jardim, Guilherme A. M.,Ferreira, Marco A. B.
, p. 3923 - 3942 (2021/04/02)
Herein, we report the synthesis of 3-carbonyl-trisubstituted furans via Pd-catalyzed oxidative cycloisomerization reactions of 2-alkenyl-1,3-dicarbonyl scaffolds, using molecular oxygen as the sole oxidant to regenerate active palladium catalytic species, featuring good functional tolerance and mild reaction conditions. Deep investigation of intermediates and transition states of the reaction mechanism were conducted via experimental and DFT studies, providing a detailed mechanistical profile. The new developed methodology presents a greener alternative to Wacker-type cycloisomerizations and avoids the use of stoichiometric amounts of oxidants and strong acid additives.
Allyl Dibenzoylmethane Derivative: Antimelanoma Activity and Study of Its Molecular Mechanism of Interaction with DNA
Andrade, Ulisses M. S.,Baeta, Jefferson V. P. B.,Diaz, Marisa A. N.,Diaz-Mu?oz, Gaspar,Oliveira, Leandro,Oliveira, Rayane M.,Rocha, Márcio S.,Santos, Anésia A.
, p. 1491 - 1497 (2021/06/15)
In this study, we assessed the cytotoxic effect of 1,3-diphenyl-2-allyl-1,3-propanedione (DPAP) on B16F10 and Tm5 melanoma cells and investigated its interaction with DNA (deoxyribonucleic acid) using optical tweezers. The compound showed to be effective
Phosphine-Catalyzed Synthesis of 3-Allyl-4-pyrones by the Tandem Reaction of Diynones and Allylic Alcohols
Fu, Ji-Ya,Wang, Yan-Bo,Yang, Wan-Wan,Ye, Ya-Fang,Zhang, Jing-Wen,Zhu, Jun-Yan
supporting information, p. 14476 - 14484 (2021/11/12)
A simple and effective tandem reaction of diynones and allylic alcohols was developed to afford functionalized 3-allyl-4-pyrones in moderate to excellent yields. This protocol underwent a Michael addition-Claisen rearrangement-O-cyclization process, which exhibited broad substrate tolerance, high regioselectivity, and atom economy under a metal-free condition. Moreover, functional transformation of the products was also further studied.
Nucleophilic Addition to π-Allyl Gold(III) Complexes: Evidence for Direct and Undirect Paths
Rodriguez, Jessica,Holmsen, Marte Sofie Martinsen,García-Rodeja, Yago,Sosa Carrizo, E. Daiann,Lavedan, Pierre,Mallet-Ladeira, Sonia,Miqueu, Karinne,Bourissou, Didier
, p. 11568 - 11581 (2021/08/20)
π-Allyl complexes play a prominent role in organometallic chemistry and have attracted considerable attention, in particular the π-allyl Pd(II) complexes which are key intermediates in the Tsuji-Trost allylic substitution reaction. Despite the huge interest in π-complexes of gold, π-allyl Au(III) complexes were only authenticated very recently. Herein, we report the reactivity of (P,C)-cyclometalated Au(III) π-allyl complexes toward β-diketo enolates. Behind an apparently trivial outcome, i.e. the formation of the corresponding allylation products, meticulous NMR studies combined with DFT calculations revealed a complex and rich mechanistic picture. Nucleophilic attack can occur at the central and terminal positions of the π-allyl as well as the metal itself. All paths are observed and are actually competitive, whereas addition to the terminal positions largely prevails for Pd(II). Auracyclobutanes and π-alkene Au(I) complexes were authenticated spectroscopically and crystallographically, and Au(III) σ-allyl complexes were unambiguously characterized by multinuclear NMR spectroscopy. Nucleophilic additions to the central position of the π-allyl and to gold are reversible. Over time, the auracyclobutanes and the Au(III) σ-allyl complexes evolve into the π-alkene Au(I) complexes and release the C-allylation products. The relevance of auracyclobutanes in gold-mediated cyclopropanation was demonstrated by inducing C-C coupling with iodine. The molecular orbitals of the π-allyl Au(III) complexes were analyzed in-depth, and the reaction profiles for the addition of β-diketo enolates were thoroughly studied by DFT. Special attention was devoted to the regioselectivity of the nucleophilic attack, but C-C coupling to give the allylation products was also considered to give a complete picture of the reaction progress.
Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons
Hemric, Brett N.,Chen, Andy W.,Wang, Qiu
, p. 1468 - 1488 (2019/01/25)
Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.
Electrochemical oxidative cyclization of olefinic carbonyls with diselenides
Guan, Zhipeng,Wang, Yunkun,Wang, Huamin,Huang, Yange,Wang, Siyuan,Tang, Hongding,Zhang, Heng,Lei, Aiwen
, p. 4976 - 4980 (2019/09/30)
The tandem cyclization of olefinic carbonyls with easily accessible diselenides facilitated by electrochemical oxidation has been successfully developed, which provides an environmentally friendly method for the construction of C-Se and C-O bonds simultaneously. A series of seleno dihydrofurans and seleno oxazolines, bearing fragile heterocycles, subtle C-I bonds and supernumerary vinyl groups, were forged using this elegant chelation strategy. Neither metal catalysts nor external chemical oxidants are required to promote this transformation.
Silica Support-Enhanced Pd-Catalyzed Allylation Using Allylic Alcohols
Motokura, Ken,Ikeda, Marika,Kim, Minjune,Nakajima, Kiyotaka,Kawashima, Sae,Nambo, Masayuki,Chun, Wang-Jae,Tanaka, Shinji
, p. 4536 - 4544 (2018/09/21)
Although allylation using allylic alcohol is an environmentally-friendly method because of water being the sole byproduct in such reactions, allylic alcohol is one of the most difficult allylating agents in Pd-catalyzed allylation of nucleophiles. In this study, we successfully developed a mesoporous silica-supported Pd complex as an efficient catalyst for the allylation of nucleophiles using allylic alcohols as allylating agents. The allylic alcohol is activated by the silanol group on the support surface, which easily undergoes a π-allylpalladium intermediate formation. The catalytic activity of the supported Pd complex was ca. 9 times higher than that of its homogeneous precursor Pd complex. A highest turnover number of 4500 based on Pd was achieved. Various nucleophiles and allylic alcohol derivatives could be used as substrates. Not only the detailed catalyst structure but also the reaction mechanism including the concerted activation of allylic alcohol by the Pd complex and silanol were investigated by several spectroscopic techniques, such as Pd K-edge XAFS, solid-state NMR, and in-situ FT-IR measurements.
Direct Allylation of Active Methylene Compounds with Allylic Alcohols by Use of Palladium/Phosphine-Borane Catalyst System
Shimizu, Aika,Hirata, Goki,Onodera, Gen,Kimura, Masanari
supporting information, p. 1954 - 1960 (2018/04/11)
The C?C bond formation between active methylene compounds and allylic alcohols has been newly developed by using a palladium complex as a catalyst together with a phosphine-borane ligand. The best phosphine-borane ligand for this direct allylation has bee
