126356-05-6Relevant articles and documents
Sm/I2-mediated selective cleavage of the S-S or C-S bonds of sodium (Z)-allyl thiosulfates in aqueous media: Selective formation of di(Z-allyl) bisulfides or (2E)-methyl cinnamic esters
Liu, Yunkui,Zheng, Hui,Xu, Danqian,Xu, Zhenyuan,Zhang, Yongmin
, p. 2492 - 2494 (2006)
Selective cleavage of the S-S or C-S bonds in sodium (Z)-allyl thiosulfates in the presence of a Sm/I2-system was achieved to form the corresponding di(Z-allyl) disulfides or (2E)-methyl cinnamic esters in moderate to good yields in aqueous med
Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
Ojha, Subhadra,Panda, Niranjan
supporting information, p. 1292 - 1298 (2022/02/19)
A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
Mizoroki–Heck Cross-Coupling of Acrylate Derivatives with Aryl Halides Catalyzed by Palladate Pre-Catalysts
Islam, Mohammad Shahidul,Nahra, Fady,Tzouras, Nikolaos V.,Barakat, Assem,Cazin, Catherine S. J,Nolan, Steven P.,Al-Majid, Abdullah Mohammed
supporting information, p. 4695 - 4699 (2019/11/13)
The Mizoroki–Heck (MH) reaction involving aryl halides with various acrylates and acrylamides has been studied using air and moisture-stable imidazolium-based palladate pre-catalysts. These pre-catalysts can be converted into Pd-NHC species (NHC = N-heterocyclic carbene) under catalytic conditions and are capable of facilitating the Mizoroki–Heck reaction of aryl halides with various acrylates. The effects of solvent, catalyst loading, temperature and bases on the reaction outcome have been investigated. Various coupling partners were tolerated under the optimal reaction conditions catalyzed by palladate 1, [SIPr·H][Pd(η3-2-Me-allyl)Cl2]. The efficiency of the optimized synthetic methodology was tested on various aryl halides and substituted acrylates as well as acrylamides. The MH reaction yielded the coupled products in good to excellent isolated yields (up to 98%).
Piperidine-appended imidazolium ionic liquid as task-specific basic-IL for Suzuki and Heck reactions and for tandem Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck protocols
Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
, p. 150 - 161 (2017/06/30)
Facile, high yielding, one-pot methods for the synthesis of a library of diversely substituted bi-aryls, diarylethenes, and aryl-enoates, via Suzuki and Heck reactions, and by sequential Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck reactions are reported. The reactions employ piperidine-appended imidazolium ionic liquid [PAIM][NTf2] as a task-specific basic-IL, butyl-methyl-imidazolium ionic liquid [BMIM][X] (X?=?PF6, BF4) as solvent, and catalytic amounts of Pd(OAc)2 with no other additives. Wittig and Horner-Emmons reactions are effected by reacting substituted benzaldehydes with 4-bromobenzyl-PPh3 (or bromomethyl-PPh3) phosphonium salts, or diethylphosphonate with bromobenzaldehydes respectively, to form the corresponding ethenes. Subsequent cross-coupling reactions are accomplished by addition of aryl-boronic acid or phenyl-ethenes along with Pd(OAc)2 to bring about the aforementioned hyphenated transformations. The feasibility to perform double-olefination via Wittig and Horner-Emmons reactions with dialdehydes to form highly conjugated bis-styryl and bis-enoate compounds is also shown. The [BMIM][X] solvent is recycled and reused.
Palladium(II) supported on polycarbosilane: Application as reusable catalyst for Heck reaction
Mangala, Kunniyur,Sinija,Sreekumar, Krishnapillai
, p. 87 - 92 (2015/07/07)
Heck reaction catalyzed by palladium(II) attached polycarbosilane is reported. Polycarbosilane (PCS), which is an organic-inorganic hybrid polymer containing both Si and C in its back bone structure, was synthesized by the polycondensation of trichloromethylsilane and trimethoxyvinylsilane in the presence of sodium metal. Palladium acetate was attached to the polycarbosilane (Pd-PCS) and its catalytic activity was investigated. Heck reaction in which C-C coupling between aryl halides or vinyl halides and activated alkenes in the presence of a base has been selected for the study. Palladium ions supported on PCS have been used as a catalyst for the first time and it efficiently catalyzed Heck reaction and an yield of 75-90% was obtained with different substrates. For comparison, catalytic activities of Pd ions supported on SBA-15, activated charcoal and amorphous silica were also investigated. Results indicate the superior activity of Pd-PCS.
Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts
Meier, Lidiane,Ferreira, Misael,Sa, Marcus M.
, p. 179 - 186 (2012/07/14)
A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO 3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence of hydrides and reducing agents.
Biopolymer-metal complex wool-Pd as a highly active heterogeneous catalyst for Heck reaction in aqueous media
Wu, Shang,Ma, Hengchang,Jia, Xiaojie,Zhong, Yunmei,Lei, Ziqiang
experimental part, p. 250 - 256 (2011/02/27)
Heterogeneous palladium catalysts, a biopolymer complex wool-Pd, have been applied in water-mediated coupling reactions of aryl bromides without assistance of any phosphine ligands. The catalyst was characterized by XPS, ICP. The results showed that aryl bromides could carry out the coupling reaction with a variety of alkenes at 80 °C, in aqueous media under atmospheric condition. More importantly, the cheap catalyst is stable, which shows negligible metal leaching, and retain good activity for at least ten successive runs without any additional activation treatment. This approach would be very useful from a practical viewpoint.
Stereoselective synthesis of trisubstituted alkenes containing (Z)-allylthio units from the acetates of Baylis-Hillman adducts
Liu, Yunkui,Xu, Danqian,Xu, Zhenyuan,Zhang, Yongmin
, p. 188 - 198 (2008/09/18)
A series of trisubstituted alkenes containing (Z)-allylthio moieties as key structural units, that is, sodium (Z)-allyl thiosulfates, symmetrical di(Z-allyl) sulfides, and di(Z-allyl) disulfides, unsymmetrical diallyl sulfides were prepared in moderate to
Sm/HOAc/EtOH system-mediated reduction of Baylis-Hillman acetates
Liu, Yunkui,Mao, Dajie,Xu, Danqian,Xu, Zhenyuan,Zhang, Yongmin
, p. 4389 - 4397 (2008/03/14)
Selective formation of (2E)-2-methylalk-2-enoates or 2-methyl alkanoates could be achieved in moderate to good yields under mild conditions via Sm/HOAc/EtOH system-mediated reduction of Baylis-Hillman acetates depending on the amount of samarium consumed in the reactions. Copyright Taylor & Francis Group, LLC.
Samarium metal promoted facile C-acetylation of Baylis-Hillman adducts in the presence of iron(III) chloride and iodine
Li, Shaoyu,Li, Jian,Jia, Xueshun
, p. 1115 - 1117 (2008/03/11)
A novel and efficient strategy for the C-acetylation of Baylis-Hillman adducts has been described. Promoted by Sm(0)/Ac2O/FeCl 3/I2, the present method allows for the efficient conversion of Morita-Baylis-Hillman adducts t
