81121-63-3Relevant articles and documents
Synthesis and evaluation of Naphthalene-1, 8-dithiolate chelating ruthenium carbene catalyst for Z-Stereoretentive olefin metathesis
Wang, Tao,Xie, Qingxiao,Guo, Weijie,Wu, Shutao,Zhang, Huiqing,Wang, Jianhui
, p. 62 - 67 (2019)
A highly Z-stereoretentive olefin metathesis ruthenium carbene catalyst containing a naphthalene-1,8-dithiol ligand was synthesized, and the structure was determined by single-crystal X-ray diffraction. The new ruthenium carbene catalyst could catalyze cross-metathesis reactions of terminal alkenes with (Z)-but-2-ene-1,4-diol to give highly Z-stereoretentive products. Like to other ruthenium carbene catalysts, the new complex tolerates many different functional groups.
Synthesis and Evaluation of Ruthenium 2-Alkyl-6-mercaptophenolate Catalysts for Olefin Metathesis
Wang, Tao,Yu, Xiaobo,Zhang, Huiqing,Wu, Shutao,Guo, Weijie,Wang, Jianhui
, (2019/04/30)
A series of ruthenium carbene catalysts containing 2-sulfidophenolate bidentate ligand with an ortho-substituent next to the oxygen atom were synthesized. The molecular structure of ruthenium carbene complex containing 2-isopropyl-6-sulfidophenolate ligand was confirmed through single crystal X-ray diffraction. An oxygen atom can be found in the opposite position of the N-heterocyclic carbene (NHC) based on the steric hindrance and strong trans-effects of the NHC ligand. The ruthenium carbene catalyst can catalyze ring-opening metathesis polymerization (ROMP) reaction of norbornene with high activity and Z-selectivity and cross metathesis (CM) reactions of terminal alkenes with (Z)-but-2-ene-1,4-diol to give Z-olefin products (Z/E ratios, 70:30–89:11) in low yields (13%–38%). When AlCl3 was added into the CM reactions, yields (51%–88%) were considerably improved and process becomes highly selective for E-olefin products (E/Z ratios, 79:21–96:4). Similar to other ruthenium carbene catalysts, these new complexes can tolerate different functional groups.
A 3,4-dimercapto-3-cyclobutene-1,2-dione-chelated ruthenium carbene catalyst for: Z -stereoretentive/stereoselective olefin metathesis
Wang, Tao,Xie, Qingxiao,Guo, Weijie,Wu, Shutao,Zhang, Huiqing,Wang, Jianhui,Wu, Botao
, p. 6473 - 6483 (2019/05/24)
A ruthenium carbene catalyst chelated with a 3,4-dioxocyclobut-1-ene-1,2-dithiolate ligand was synthesized and its molecular structure was determined by single-crystal X-ray diffraction. The Ru catalyst had excellent catalytic activity with high yields and good Z/E ratios for the ring opening metathesis polymerization (ROMP) of norbornene (yield: 96%/Z/E: 86 : 14) and 1,5-cyclooctadiene (yield: 86%/Z/E: 91 : 9) and for ring opening cross metathesis (ROCM) reactions of norbornene/5-norbornene-2-exo, 3-exo-dimethanol with styrene (yields: 64%-92%/Z/E: 97 : 3-98 : 2) or 4-fluorostyrene (yield: 46%-94%/Z/E: 98 : 2). The catalyst also had high Z-stereoretentivity (91 : 9-98 : 2) for cross-metathesis (CM) reactions of terminal olefins with (Z)-2-butene-1,4-diol. More importantly, the catalyst had moderate Z-stereoselectivity for homometathesis reactions of terminal olefins giving cis-olefins as the major products (Z/E ratios of 70 : 30-77 : 23). Like other Ru carbene complexes, the catalyst tolerates many different functional groups. The presented data, supported by DFT calculations, show that our catalyst, bearing a chelating 3,4-dioxocyclobut-1-ene-1,2-dithiolate ligand, exhibits higher stability towards air than Hoveyda's stereoretentive complex systems.
Synthesis, catalysis, and DFT study of a ruthenium carbene complex bearing a 1,2-dicarbadodecaborane (12)-1,2-dithiolate ligand
Wang, Tao,Wu, Botao,Guo, Weijie,Wu, Shutao,Zhang, Huiqing,Dang, Yanfeng,Wang, Jianhui
, p. 2646 - 2656 (2019/02/27)
A ruthenium carbene catalyst containing a 1,2-dicarbadodecaborane(12)-1,2-dithiolate ligand was synthesized, and the structure was determined by single crystal X-ray diffraction. This new ruthenium carbene catalyst can catalyze the ring opening metathesis polymerization (ROMP) reaction of norbornene to give the corresponding Z-polymer (Z/E ratio, 98:2) in high yield (93%); ring opening cross metathesis (ROCM) reactions of norbornene/5-norbornene-2-exo, 3-exo-dimethanol with styrene or 4-fluorostyrene to give the corresponding Z-olefin products (Z/E ratios, 97:3-98:2), respectively, in high yields (73%-88%); cross metathesis (CM) reactions of terminal alkenes with (Z)-but-2-ene-1,4-diol to give high Z-olefin products in low yields; homometathesis reactions of terminal alkenes to give olefin products in low yields. Like other ruthenium carbene catalysts, the new complex tolerates many different functional groups. DFT calculations were also performed in order to understand the process of forming Z-olefin products and the decomposition process of catalysts.
The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex
Mukherjee, Paramita,Widenhoefer, Ross A.
supporting information, p. 3437 - 3444 (2013/07/05)
A 1:1 mixture of [AuCl(IPr)] (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidine) and AgClO4 catalyzes the intermolecular dehydrative alkoxylation of primary and secondary allylic alcohols with aliphatic primary and secondary alcohols to for
Palladium-catalyzed 1,4-addition of carboxylic acids to butadiene monoxide
Hamasaki, Akiyuki,Maruta, Shuhei,Nakamura, Aki,Tokunaga, Makoto
supporting information, p. 2129 - 2134 (2012/11/07)
Palladium complexes catalyze the 1,4-addition of acetic acid to butadiene monoxide to give 4-hydroxybut-2-en-1-yl acetate. The highest 1,4-/1,2-addition selectivity of 18.9 was achieved. The reaction seems to proceed via a Wacker-like mechanism. Copyright
Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization
Ragoussi, Maria-Eleni,Walker, Stephen M.,Piccanello, Andrea,Kariuki, Benson M.,Horton, Peter N.,Spencer, Neil,Snaith, John S.
supporting information; experimental part, p. 7347 - 7357 (2011/02/16)
A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto α,β-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2
Nazarov approach to 4-benzoyloxymethyl-cyclopent-2-enone, a precursor to the helminthosporols
Belardi, Justin K.,Curtis, Lindsay A.,Clareen, Steven S.,Shimp, Heidi L.,Leimkuhler, Catherine E.,Simonowicz, Nicole L.,Casillas, Eduard
, p. 1633 - 1640 (2007/10/03)
A short, scalable route to 4-hydroxymethylcyclopent-2-enone, based upon a silicon-directed Nazarov cyclization, is described. Noteworthy in this study is the success of the cyclization with an oxygenated substrate. Copyright Taylor & Francis, Inc.
Lipase-catalyzed monoprotection of 1,4-diols in an organic solvent using vinyl benzoate as acyl transfer agent
Ciuffreda, Pierangela,Casati, Silvana,Santaniello, Enzo
, p. 3663 - 3665 (2007/10/03)
Lipase from Mucor miehei (MML) has been selected as the most suitable enzyme to catalyze the efficient monobenzoylation of 1,4-diols using vinyl benzoate as acyl transfer reagent in tert-butyl methyl ether. The regioselectivity of the monobenzoylation of
Selective Deprotection of tert-Butyldimethylsilyl Ethers Using Nafion-H/Sodium Iodide (or Bromodimethylsulfonium Bromide) in Methanol
Rani, Shikha,Babu, J. Lokesh,Vankar, Yashwant D.
, p. 4043 - 4052 (2007/10/03)
Catalytic amounts of bromodimethyl sulfonium bromide, or Nafion-H along with NaI (1 equiv.), in methanol cleave a variety of TBDMS ethers readily in high yields. Alkyl TBDMS ethers react more readily and selectively compared to phenolic TBDMS ethers, benzyl, and methyl ethers.
