218591-03-8Relevant academic research and scientific papers
Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates
Yan, Tingting,Babu, Kaki Raveendra,Wu, Yong,Li, Yang,Tang, Yuhai,Xu, Silong
supporting information, p. 4570 - 4574 (2021/06/28)
A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.
Benign Arylations of Dimethyl Itaconate via Heck–Matsuda Reaction Utilizing in-Situ Generated Palladium on Aluminum Oxide
Matelien?, Lauryna,Knaup, Jan,von Horsten, Frank,Gu, Xiaoting,Brunner, Heiko
supporting information, p. 127 - 135 (2020/01/30)
In situ generated palladium on aluminum oxide provides an active and efficient catalytic system for the preparation of arylmethylidene succinates using the Heck–Matsuda reaction. Beside the monoarylation the first examples of the biarylation of these mono
Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes
Bangar, Pronnoy G.,Jawalkar, Priyanka R.,Dumbre, Swapnil R.,Patil, Dharmaraj J.,Iyer, Suresh
, (2017/11/23)
A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the Mizoroki-Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.
Novel Base-Free Catalytic Wittig Reaction for the Synthesis of Highly Functionalized Alkenes
Schirmer, Marie-Luis,Adomeit, Sven,Spannenberg, Anke,Werner, Thomas
supporting information, p. 2458 - 2465 (2016/02/12)
A highly efficient catalyst system for base-free catalytic Wittig reactions has been developed and optimized. Initially, several potential (pre)catalysts as well as different silanes as reducing agents were screened. A system based on a readily available
Tris(4-anisyl)phosphine as an efficient and practical reagent for the synthesis of (E)-2-benzylidenesuccinates
Jiang, Huanfeng,Wang, Wei,Liu, Weibing,Qiao, Chunli
experimental part, p. 263 - 268 (2010/10/21)
Condensation of maleic anhydride or dimethyl maleate with benzylaldehydes controlled by tris(4-anisyl)-phosphine to synthesize dimethyl (E)-2-benzylidenesuccinates has been systematically investigated. The protocol gives the product with high stereoselectivity in moderate to good yields under mild conditions. A plausible mechanism has been proposed.
Process research on arylnaphthalene lignan aza-analogues: a new palladium-catalyzed benzannulation of α,β-bisbenzylidenesuccinic acid derivatives
Mizufune, Hideya,Nakamura, Minoru,Mitsudera, Hiroyuki
, p. 8539 - 8549 (2007/10/03)
The discovery of a new Pd-catalyzed benzannulation reaction of bisbenzylidenesuccinimide during process research on arylnaphthalene lignan aza-analogues is described. An extension of the Pd-catalyzed benzannulation to the regiospecific synthesis of variou
Efficient Heck arylations of cyclic and acyclic acrylate derivatives using arenediazonium tetrafluoroborates. A new synthesis of the antidepressant drug (±)-paroxetine
Pastre, Julio Cezar,Correia, Carlos Roque Duarte
, p. 1657 - 1660 (2007/10/03)
The Heck arylation of acyclic- and cyclic-substituted acrylates using several arenediazonium tetrafluoroborates was investigated. Arylations were carried out under aerobic, ligand-free conditions to provide the corresponding substituted acrylates in moderate to high isolated yields. Heck arylations were usually completed in less than 2 h in refluxing methanol. The aza-endocyclic acrylate derivative 11a was converted into the antidepressant drug (±)-paroxetine in a concise new route in good overall yield.
Unexpected reaction of dimethyl acetylenedicarboxylate with in situ generated arylketenes catalyzed by 1-methylimidazole
Ding, Hanfeng,Ma, Cheng,Yang, Yewei,Wang, Yanguang
, p. 2125 - 2127 (2007/10/03)
(Chemical Equation Presented) An unexpected 1-methylimidazole-catalyzed reaction of dimethyl acetylenedicarboxylate (DMAD) with in situ generated arylketenes leading to the synthesis of dimethyl 2-arylidenesuccinates under mild conditions is described. A plausible mechanism has been proposed.
Sequential Transformation of Diethyl Phosphite. A Convenient Synthesis of Substituted (E)-3-Alkoxycarbonyl-β,γ-unsaturated Esters
Shen, Yanchang,Zhang, Zenghong
, p. 642 - 643 (2007/10/03)
The sequential reaction of diethyl phosphite with sodium alkoxide, dimethyl maleate and aldehydes affords substituted (E)-3-alkoxycarbonyl-β,γ-unsaturated esters in 63-73% yields.
