100891-10-9Relevant articles and documents
An efficient palladium catalyzed Mizoroki-Heck cross-coupling in water
Jadhav, Sanjay N.,Rode, Chandrashekhar V.
, p. 5958 - 5970 (2017)
The homogeneous Pd-catalysed Mizoroki-Heck coupling reaction was successfully performed in water in the absence of any additives under aerobic conditions. The various key reaction parameters that affect the yield of the desired cross-coupling product were optimized. The Pd(PPh3)4/Et3N/H2O/98 °C catalyst system was found to be highly active (TOF = 12 to 14 h-1) towards achieving excellent yield of the Mizoroki-Heck coupling products for a wide range of electron-withdrawing as well as electron-donating aryl bromides and chlorides in the shortest reaction time. Pd(PPh3)4 catalyst deactivation during the Mizoroki-Heck coupling reaction was investigated and to evolve a strategy for achieving ten times Pd-metal recyclability without appreciable loss of its activity. Thus, the proposed mechanism provides access to a variety of olefins in aqueous medium, making this protocol eco-friendly.
An ionic liquid catalyzed probase method for one-pot synthesis of α,β-unsaturated esters from esters and aldehydes under mild conditions
Wang, Gang,Xu, Yiming,Zhang, Suojiang,Li, Zengxi,Li, Chunshan
, p. 4838 - 4848 (2017)
A one-pot synthesis of α,β-unsaturated esters from unactivated esters and aldehydes using strong bases, such as sodium alkoxide and potassium tert-butoxide, was reported. However, the ionic liquid (IL) catalyzed probase method for producing α,β-unsaturated esters was not reported until now. In this work, a series of ILs with fluoride anions were firstly prepared and used as catalysts in combination with the probase N,O-bis(trimethylsilyl) acetamide (BSA) for the α,β-unsaturated esters synthesis. This process could also be promoted through the introduction of another IL with Lewis acid sites. The yield and selectivity of the product could reach up to 84.2% and 95.0%, respectively, when [Bmim]F was used in combination with [Bmim]Cl/AlCl3 (the molar fraction of AlCl3 is 0.67). The mechanism investigation through GC-MS indicates that BSA would convert into onium amide, which acted as a strong base for α-H abstraction, with the catalysis of [Bmim]F. Meanwhile, [Bmim]Cl/AlCl3 played an important role in the condensation step between enolates and aldehydes. On the basis of mechanism insights, kinetic and thermodynamic studies were also carried out for a better understanding of this new route.
The ligand and base-free Pd-catalyzed oxidative Heck reaction of arylboronic acids and olefins
Sun, Peng,Zhu, Yan,Yang, Hailong,Yan, Hong,Lu, Linhua,Zhang, Xiang,Mao, Jincheng
, p. 4512 - 4515 (2012)
Highly effective Pd-catalyzed Heck-type oxidative couplings between arylboronic acids and terminal olefins were reported. It is noteworthy that such reactions could be carried out in the absence of the base and the ligand.
Acyclic diaminocarbenes: Simple, versatile ligands for cross-coupling reactions
Dhudshia, Bhartesh,Thadani, Avinash N.
, p. 668 - 670 (2006)
Acyclic diaminocarbenes are found to be useful ligands for palladium catalyzed Suzuki-Miyaura, Sonogashira and Heck cross-coupling reactions of aryl/alkenyl bromides and chlorides. The Royal Society of Chemistry 2006.
Mizoroki–Heck cross-coupling reactions using palladium immobilized on DABCO-functionalized silica
Jadhav, Sanjay,Patil, Seema,Kumbhar, Arjun,Kamble, Santosh,Salunkhe, Rajashri
, p. 507 - 514 (2019)
A heterogeneous palladium catalyst supported on silica modified by DABCO has been prepared by post-synthetic modification of silica gel. This heterogeneous catalytic system exhibits high activity and stability in the Mizoroki–Heck cross-coupling reaction of various aryl halides with olefins. The reaction proceeds efficiently under efficiently under mild mild reaction conditions and high yield, with the formation of E-isomers selectively. Moreover, we successfully established a gram-scale synthesis, and the catalyst was reused for up to ten catalytic cycles.
Synthesis and biological evaluation of phloroglucinol derivatives possessing α-glycosidase, acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase inhibitory activity
Burmaoglu, Serdar,Yilmaz, Ali O.,Taslimi, Parham,Algul, Oztekin,Kilic, Deryanur,Gulcin, Ilhami
, (2018)
A series of novel phloroglucinol derivatives were designed, synthesized, characterized spectroscopically and tested for their inhibitory activity against selected metabolic enzymes, including α-glycosidase, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase I and II (hCA I and II). These compounds displayed nanomolar inhibition levels and showed Ki values of 1.14–3.92 nM against AChE, 0.24–1.64 nM against BChE, 6.73–51.10 nM against α-glycosidase, 1.80–5.10 nM against hCA I, and 1.14–5.45 nM against hCA II.
Pd nanoparticles in the thermoregulated ionic liquid and organic biphasic system: An efficient and recyclable catalyst for heck reaction
Zeng, Yan,Wang, Yanhua,Xu, Yicheng,Song, Ying,Jiang, Jingyang,Jin, Zilin
, p. 200 - 205 (2013)
A thermoregulated ionic liquid and organic biphasic system composed of ionic liquid [CH3(OCH2CH2)16N +Et3][CH3SO3 -] (IL PEG750) with ILPEG750-stabilized Pd nanoparticles and organic solvents, which allows for not only a highly efficient homogeneous catalytic reaction, but also an easy biphasic separation and reuse of catalyst attributed to the thermoregulated phase-transition property of the system, was employed for Heck reaction. The ILPEG750-stabilized Pd nanoparticle catalyst exhibited high efficiency, more importantly, after reaction the Pd nanoparticle catalyst could be separated from products by simple phase separation and recycled for six times without evident loss of activity. Graphical Abstract: A thermoregulated ionic liquid and organic biphasic system containing [CH3(OCH2CH2)16N +Et3][CH3SO 3 - ] (ILPEG750)-stabilized Pd nanoparticles was applied to Heck reaction for the first time. The Pd nanoparticle catalyst exhibited high efficiency and good recyclability.[Figure not available: see fulltext.]
A one-pot silyl-Reformatsky olefination
Smith, James M.,Greaney, Michael F.
, p. 8687 - 8690 (2007)
A novel one-pot olefination reaction has been developed, involving the stereoselective formation of (E)-α,β-unsaturated esters/ketones from the reaction of α-bromocarbonyl compounds with aromatic aldehydes. The reactions use a reagent combination of trichlorosilane, and triethylamine and may proceed via the in situ formation of a trichlorosilyl ketene acetal. The general procedure offers key advantages (high conversions, low quantities of organic soluble by-products) over the conventional Wittig reaction.
Immobilization of Pd nanoparticles with functional ionic liquid grafted onto cross-linked polymer for solvent-free Heck reaction
Liu, Gang,Hou, Minqiang,Song, Jiyuan,Jiang, Tao,Fan, Honglei,Zhang, Zhaofu,Han, Buxing
, p. 65 - 69 (2010)
1-Aminoethyl-3-vinylimidazolium bromide ([VAIM]Br) grafted on the cross-linked polymer polydivinylbenzene (PDVB) was synthesized. The copolymers were used as a support to immobilize palladium nanoparticles. The catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), thermogravimetric (TG) analysis, transmission electron microscopy (TEM) and X-ray photoelectron spectroscopy (XPS). The catalytic performance of the copolymer-supported Pd nanoparticles for the Heck arylation of olefins with different aryl iodides was studied under solvent-free conditions. The results demonstrated that the catalyst was very active and stable under solvent-free conditions, and could be reused after simple separation. The reason for the high activity and stability of the catalyst is discussed.
Cadmium-catalyzed olefination of aldehydes with α-bromoacetic ester in the presence of tri-n-butylarsine
Zheng,Shen
, p. 2069 - 2073 (1994)
Cadmium-catalyzed olefination of aldehydes with α-bromoacetic ester in the presence of tri-n-butylarsine is described.
