65859-90-7Relevant articles and documents
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
First Base-Free Catalytic Wittig Reaction
Schirmer, Marie-Luis,Adomeit, Sven,Werner, Thomas
supporting information, p. 3078 - 3081 (2015/06/30)
The first base-free catalytic Wittig reaction utilizing readily available Bu3P (5 mol %) as an organocatalyst is reported. The initial Michael addition of the phosphine to a suitable acceptor substituted alkene ultimately results in the formation of an ylide which is subsequently converted with an aldehyde. The presented 1H NMR studies actually reveal evidence for the Michael addition and proposed ylide formation. Under the optimized reaction conditions various maleates and fumarates were converted with aromatic, heteroaromatic, and aliphatic aldehydes to evaluate the scope and limitations of this unprecedented reaction. Notably, maleates and fumarates react in a stereoconvergent fashion. The corresponding products were obtained in up to 95% isolated yield and E/Z-selectivities up to 99:1.
Synthesis of 6-deoxymollugins and their inhibitory activities on tyrosinase
Liang, Jing Lu,Javed, Umair,Lee, Seung Ho,Park, Jae Gyu,Jahng, Yurngdong
, p. 862 - 872 (2014/08/05)
A series of 6-deoxymollugins were prepared five steps from benzaldehyde and its derivatives via phenylboronic acid-catalyzed chromenylation as a key step. Their inhibitory activities against tyrosinase from mushroom were evaluated to show that the parent,
Regioselective monoalkylation of dimethyl alkylidenesuccinates: Simple approach to dialkyl-substituted maleic anhydrides including chaetomellic acid A
Kshirsagar, Umesh A.,Argade, Narshinha P.
experimental part, p. 1804 - 1808 (2011/07/29)
Natural and nonnatural dialkylmaleic anhydrides were readily prepared from dimethyl alkylidenesuccinates by sodium hexamethyldisilazide-induced selective monoalkylation followed by base-catalyzed hydrolysis. Georg Thieme Verlag Stuttgart - New York.
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.
Practical synthetic method of (2Z,3E)-1,4-Diphenylbutadiene T-2639, an inhibitor of plasminogen activator inhibitor-1 (PAI-1) production
Miyazaki, Hiroshi,Ohmizu, Hiroshi,Ogiku, Tsuyoshi
scheme or table, p. 760 - 763 (2010/04/22)
A practical synthetic method of (2Z,3E)-1,4-diphenylbutadiene derivative T-2369 (1), a potent inhibitor of plasminogen activator inhibitor-1 (PAI-1) production, is described. Conditions of Stobbe condensation in the conventional synthesis of T-2369 were e
A new target for highly stereoselective Katsuki-Sharpless epoxidation - One-pot synthesis of C2-symmetric 2,2′-bioxiranes
Bilenko, Vitaliy,Jiao, Haijun,Spannenberg, Anke,Fischer, Christine,Reinke, Helmut,Koesters, Jutta,Komarov, Igor,Boerner, Armin
, p. 758 - 767 (2008/02/07)
The double asymmetric Katsuki-Sharpless epoxidation of a conjugated diallyl alcohol affords excellent enantioselectivity (>97% ee), the product being isolated as the stable p-nitrobenzoate 5a or tosylate 5b. The optical purities of the chiral epoxides were determined by HPLC on chiral columns, while the molecular structures of compounds 5a and 7 and the absolute configuration of mono-epoxide 12 were confirmed by X-ray crystallography. Possible π-π stacking interaction has been evaluated by ab initio calculation. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
