36854-27-0Relevant articles and documents
Analysis of the 13C and 1H Spectra of Mixtures of Benzylidene Derivatives
Bradley, J. C.,Williams, A. J.
, p. 496 - 498 (1994)
The 1H and 13C NMR spectra of methyl (E)-2,3-diphenylprop-2-enoate and methyl (E)-2-(2-phenylethenyl)benzoate resulting from the electrocyclic ring opening of benzocyclobutenone starting materials have been assigned.A combination of direct detection 2D NMR techniques, COSY, HETCOR, and FLOCK, provided the assignments of the 1H and 13C resonances. - Keywords: NMR 1H NMR 13C NMR Benzylidene derivatives
Magnesium chloride (MgCl2) catalyzed highly regioselective C-3 ring opening of 2,3 epoxy alcohols by N-nucleophile
Kumar, Amit,Panda, Gautam
supporting information, (2021/04/09)
We herein report Magnesium chloride (MgCl2) catalyzed first highly C3-selective ring-opening reaction of various 2,3-epoxy alcohols with assorted N-Nucleophiles and sodium azide to furnish 3-amino-1,2 diols and 3-azido-1,2 diols respectively in high yields under mild reaction conditions. This protocol attributes the use of catalytic amount of Magnesium chloride (MgCl2), simple reaction conditions, practical operation and broad functional group tolerance.
Polysubstituted ethylene compound as well as preparation method and application thereof
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Paragraph 0125-0129; 0230-0234, (2020/12/30)
The invention discloses a polysubstituted ethylene compound as well as a preparation method and application thereof. The invention particularly discloses a preparation method of a polysubstituted ethylene compound as shown in a formula III, which comprises the following step: in an organic solvent, carrying out reaction as shown in the specification on a compound as shown in a formula I and a compound as shown in a formula II in the presence of a palladium catalyst, a phosphine ligand and alkali to obtain the polysubstituted ethylene compound as shown in the formula III. The preparation methodcan be suitable for various types of substrates, and the configuration of double bonds is controllable.
Oxiranyl remote anions from epoxy cinnamates and their application towards the synthesis of α,β-epoxy-γ-butyrolactones
Sermmai, Patpanat,Ruangsupapichat, Nopporn,Thongpanchang, Tienthong
supporting information, (2020/11/19)
A series of α,β-epoxy-γ-butyrolactones were synthesized in moderate yields via oxiranyl remote anions derived from epoxy cinnamate esters. The key synthetic step involved deprotonation of the β-position of α,β-epoxy cinnamate derivatives where the generated β-anion was stabilized by remote chelation from an ester group. The substitution reaction of the anion with a variety of ketones, followed by cyclization, readily furnished the desired substituted α,β-epoxy-γ-butyrolactones.
Rhodium-Catalyzed Carbene Transfer Reactions for Sigmatropic Rearrangement Reactions of Selenium Ylides
Jana, Sripati,Koenigs, Rene M.
, p. 3653 - 3657 (2019/05/24)
The rearrangement of selenium ylides is even today almost unexplored, although it would provide access to important organoselenium compounds with broad downstream applications. In this report, the first systematic study of sigmatropic rearrangement reactions of selenium ylides using a simple rhodium catalyst with catalyst loadings as low as 0.01 mol % is described. Selenium oxide pyrolysis of the rearrangement products gives access to important 1,1-disubstituted butadienes.
Nickel nanoparticle-catalyzed carboxylation of unsaturated hydrocarbon with CO2 using sulfur-modified Au-supported nickel material
Taniguchi, Takahisa,Saito, Nozomi,Doi, Ryohei,Kimoto, Arato,Hoshiya, Naoyuki,Fujiki, Katsumasa,Shuto, Satoshi,Fujioka, Hiromichi,Arisawa, Mitsuhiro,Sato, Yoshihiro
supporting information, p. 1406 - 1409 (2019/11/05)
A hydrocarboxylation reaction of alkyne or styrene derivatives with CO2 proceeded smoothly by using an air-stable nano-sized nickel catalyst supported on sulfur-modified gold (SANi), giving functionalized acrylic acids and phenylpropionic acids including an anti-inflammatory drug, Flurbiprofen. Notably, SANi could be recycled several times without a significant decrease of the yield.
A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters by tandem acetylation-E1CB reaction
Ozeki, Minoru,Hachino, Ayumi,Shigeta, Takashi,Niki, Aya,Kobayashi, Natsuko,Mizutani, Hideki,Nakamura, Akihiro,Horie, Ayano,Arimitsu, Kenji,Kajimoto, Tetsuya,Hosoi, Shinzo,Iwasaki, Hiroki,Kojima, Naoto,Yamashita, Masayuki,Kawasaki, Ikuo
, p. 71 - 74 (2019/01/17)
A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters was developed by improving our previously established method. The new method circumvented the separation of the intermediates, which have an activating group of the hydroxyl group in β-hydroxy esters, furnishing α,β-unsaturated esters in shorter steps than the previous method: an acetylation of β-hydroxy group and subsequent E1cB reaction proceeded in tandem. In addition, the new method can not only employ a diastereomeric mixture of the substrate for the E1cB reaction, it has a wide substrate scope as well, which would enable the synthesis of various trisubstituted (E)-α,β-unsaturated esters.
Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones
Huang, David,Szewczyk, Suzanne M.,Zhang, Pengpeng,Newhouse, Timothy R.
supporting information, p. 5669 - 5674 (2019/04/26)
We herein disclose the first report of a first-row transition metal-catalyzed α,β-dehydrogenation of carbonyl compounds using allyl-nickel catalysis. This development overcomes several limitations of previously reported allyl-palladium-catalyzed oxidation, and is further leveraged for the development of an oxidative cycloalkenylation reaction that provides access to bicycloalkenones with fused, bridged, and spirocyclic ring systems using unactivated ketone and alkene precursors.
Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters
Liu, Jiawang,Dong, Kaiwu,Franke, Robert,Neumann, Helfried,Jackstell, Ralf,Beller, Matthias
supporting information, p. 10282 - 10288 (2018/08/03)
A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.
