Jump to Main Content
PubAg
Main content area
Search
« Previous |
1 - 20 of 60
|
Next »
Search Results
- Author:
- Mari, Daichi; Miyagawa, Naoki; Okano, Kentaro; Mori, Atsunori
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14126-14137
- ISSN:
- 1520-6904
- Subject:
- deprotonation; halogens; lithium; moieties; organic chemistry; organic compounds; positional isomers
- Abstract:
- ... The LDA (lithium diisopropylamide)-promoted regiocontrolled halogen dance of α-bromothiophenes and α-bromofurans is described. Bromothiophenes bearing a diethyl acetal moiety undergo selective deprotonation at the β-position adjacent to the bromo group. In contrast, oxazoline, ester, and amide groups act as directing groups in the initial lithiation step to generate a carbanion at the β-position n ...
- DOI:
- 10.1021/acs.joc.8b02220
-
http://dx.doi.org/10.1021/acs.joc.8b02220
- Author:
- Zhao, Yue; Lin, Jin-Hong; Hang, Xiao-Chun; Xiao, Ji-Chang
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14120-14125
- ISSN:
- 1520-6904
- Subject:
- chemical reactions; chemical structure; organic chemistry; organic compounds; protocols
- Abstract:
- ... Ag-mediated trifluoromethylthiolation of inert Csp³–H bond with CF₃SOCl is described. Widely available reagents and operational simplicity make this protocol attractive. ...
- DOI:
- 10.1021/acs.joc.8b02207
-
http://dx.doi.org/10.1021/acs.joc.8b02207
- Author:
- Tang, Ren-Jin; Milcent, Thierry; Crousse, Benoit
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14001-14009
- ISSN:
- 1520-6904
- Subject:
- alcohols; aromatic hydrocarbons; benzylation; catalysts; chemical structure; hydrogen bonding; organic chemistry; regioselectivity; sulfates
- Abstract:
- ... We report here a method of direct Friedel–Crafts benzylation of arenes with benzylic alcohols using cheap and readily available bisulfate salt as the catalyst in hexafluoroisopropanol. The catalytic system is powerful with a quite diverse group of functionalized arenes and benzylic alcohols. These mild conditions provide a straightforward synthesis of a variety of unsymmetrical diarylmethanes in h ...
- DOI:
- 10.1021/acs.joc.8b02361
-
http://dx.doi.org/10.1021/acs.joc.8b02361
- Author:
- Xie, Shengling; Ren, Pan; Hou, Jieping; Ning, Chengqing; Xu, Jing
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14152-14157
- ISSN:
- 1520-6904
- Subject:
- chemical reactions; chemical structure; organic chemistry; organic compounds; stereoselective synthesis; stereoselectivity
- Abstract:
- ... Aspterpenacids A and B are sesterterpenoids that possess a unique and highly congested 5/3/7/6/5 fused ring system. These compounds also contain a sterically encumbered isopropyl trans-hydrindane motif and a cyclopropane motif bearing two quaternary centers, which make them remarkably challenging synthetic targets. Herein, we report the successful construction of the key highly substituted ABC rin ...
- DOI:
- 10.1021/acs.joc.8b02263
-
http://dx.doi.org/10.1021/acs.joc.8b02263
- Author:
- Inagaki, Sho; Saito, Kai; Suto, Soichiro; Aihara, Hiromi; Sugawara, Aoi; Tamura, Satoru; Kawano, Tomikazu
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13834-13846
- ISSN:
- 1520-6904
- Subject:
- chemical structure; cost effectiveness; cyclization reactions; organic chemistry; organic compounds; salts
- Abstract:
- ... Base-induced intramolecular cyclization of novel (4-aryl-2,4-dioxobutyl)methylphenylsulfonium salts prepared from the commercially available 1-arylethanone by a cost-effective process is described in this paper. The reaction was completed within 10 min to produce a family of 2-unsubstituted 5-aryl-3(2H)-furanones in excellent yield. This procedure is simple, and can be carried out under mild condi ...
- DOI:
- 10.1021/acs.joc.8b02153
-
http://dx.doi.org/10.1021/acs.joc.8b02153
- Author:
- Ausekle, Elina; Ehlers, Peter; Villinger, Alexander; Langer, Peter
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14195-14202
- ISSN:
- 1520-6904
- Subject:
- arylation; benzene; catalytic activity; chemical bonding; chemical structure; organic chemistry; palladium; phenols; synthesis
- Abstract:
- ... We report base-mediated reactions of 1-bromo-2-(2,2-difluorovinyl)benzenes with phenols followed by Pd-catalyzed intramolecular C–H arylation, which offers a novel route to a pharmaceutically relevant class of compounds, oxepines. Construction of these medium-sized ring structures proceeds as a one-pot two-step reaction through diaryl ketene acetals as intermediates. It allows to obtain various di ...
- DOI:
- 10.1021/acs.joc.8b02374
-
http://dx.doi.org/10.1021/acs.joc.8b02374
- Author:
- Yu, Hui; Hu, Bin; Huang, Hanmin
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13922-13929
- ISSN:
- 1520-6904
- Subject:
- Lewis acids; alkenes; benzylamines; benzylation; chemical bonding; chemical structure; cleavage (chemistry); iodine; nickel; organic chemistry; oxidants
- Abstract:
- ... We have developed the first example of nickel-catalyzed Heck-type benzylation of aryl olefins with various benzylamines as benzyl electrophiles, and the benzylic C–N bond cleavage was efficiently promoted by the amine–I₂ charge transfer complex (CT complex). The combination of low-cost NiCl₂ and I₂ has been found to facilitate Heck reaction of tertiary benzylamines and alkenes into various benzyl- ...
- DOI:
- 10.1021/acs.joc.8b02279
-
http://dx.doi.org/10.1021/acs.joc.8b02279
- Author:
- Ding, Wenhuan; Zhang, Youquan; Yu, Aimin; Zhang, Lei; Meng, Xiangtai
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13821-13833
- ISSN:
- 1520-6904
- Subject:
- chemical reactions; chemical structure; organic chemistry; organic compounds; reaction mechanisms; sulfur; synthesis
- Abstract:
- ... Substrate-controlled domino reactions between thioaurones or their analogues and crotonate-derived sulfur ylides were developed and produced a broad spectrum of benzothiophene-fused pyran derivatives, substituted chromene derivatives. In these reactions, crotonate-derived sulfur ylides acting as two-carbon synthons (α and β carbons or β and γ carbons) in annulation reactions are reported for the f ...
- DOI:
- 10.1021/acs.joc.8b02152
-
http://dx.doi.org/10.1021/acs.joc.8b02152
- Author:
- Liu, Si-Wei; Gao, Ying-Juan; Shi, Yin; Zhou, Lin; Tang, Xue; Cui, Hai-Lei
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13754-13764
- ISSN:
- 1520-6904
- Subject:
- acetates; carbonates; chemical reactions; chemical structure; copper; isoquinolines; organic chemistry; quinolines
- Abstract:
- ... This study presents a convenient synthesis of pyrrolo[1,2-a]quinolines and pyrrolo[2,1-a]isoquinolines with simple quinolines or isoquinolines and Morita–Baylis–Hillman carbonates in the presence of copper acetate. A range of functionalized benzoindolizines could be assembled through an SN2′/deprotonation/1,5-electrocyclization/oxidation cascade pathway in a one-step process. ...
- DOI:
- 10.1021/acs.joc.8b02065
-
http://dx.doi.org/10.1021/acs.joc.8b02065
- Author:
- Friedrich, Ryan M.; Bell, Jay Q.; Garcia, Alfredo; Shen, Zican; Friestad, Gregory K.
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13650-13669
- ISSN:
- 1520-6904
- Subject:
- alcohols; antagonists; bioactive properties; catalytic activity; chemical reactions; diastereoselectivity; enantiomers; fibrinogen; nuclear magnetic resonance spectroscopy; organic chemistry; stereochemistry
- Abstract:
- ... Diverse classes of natural products contain chiral 1,5,9- and 1,5,7-triol stereotriads, including the novel fibrinogen receptor antagonist tetrafibricin. Biological activities associated with compounds containing these motifs warrant targeted synthetic strategies to 1,5-polyol families from cheap and easily accessible reagents while avoiding the need to determine configurations at each alcohol ste ...
- DOI:
- 10.1021/acs.joc.8b02034
-
http://dx.doi.org/10.1021/acs.joc.8b02034
- Author:
- Jiménez, Vicente G.; Santos, Fábio M. F.; Castro-Fernández, Silvia; Cuerva, Juan M.; Gois, Pedro M. P.; Pischel, Uwe; Campaña, Araceli G.
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14057-14062
- ISSN:
- 1520-6904
- Subject:
- boron; chemical reactions; circular dichroism spectroscopy; dyes; luminescence; organic chemistry; organic compounds; stereoisomers
- Abstract:
- ... Racemic mixtures of boronic acid-derived salicylidenehydrazone (BASHY) complexes were enantiomerically resolved. The chiroptical properties of the stereoisomers, containing an asymmetric boron as the only stereogenic unit, are translated into mirror-imaged electronic circular dichroism spectra and circularly polarized luminescence (CPL, dissymmetry factors of 3–5 × 10–⁴) is observed. The spectral ...
- DOI:
- 10.1021/acs.joc.8b01844
-
http://dx.doi.org/10.1021/acs.joc.8b01844
- Author:
- Lukyanov, Daniil A.; Konev, Alexander S.; Amsharov, Konstantin; Khlebnikov, Alexander F.; Hirsch, Andreas
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14146-14151
- ISSN:
- 1520-6904
- Subject:
- chemical structure; cycloaddition reactions; fullerene; nuclear magnetic resonance spectroscopy; organic chemistry; organic compounds; stable isotopes; stereochemistry
- Abstract:
- ... The diastereospecific and highly site-selective cycloaddition of N-arylazomethine ylides generated in situ from diethyl N-arylaziridine-2,3-dicarboxylates to C₇₀ fullerene is reported. The reaction provides C₇₀ fulleropyrrolidines in up to hundreds on a milligram scale as α- and β-adducts in a 4:1 ratio with a controlled stereochemical outcome: cis-aziridines give exclusively trans-adducts, and tr ...
- DOI:
- 10.1021/acs.joc.8b02240
-
http://dx.doi.org/10.1021/acs.joc.8b02240
- Author:
- Zhang, Sheng; Yamamoto, Yoshinori; Bao, Ming
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13981-13990
- ISSN:
- 1520-6904
- Subject:
- Lewis bases; catalysts; catalytic activity; chemical reactions; chemical structure; ketones; ligands; organic chemistry; palladium; regioselectivity
- Abstract:
- ... The palladium-catalyzed reaction of 1-(chloromethyl)naphthalenes 1 with (hetero)arylacetonitriles 2 gives either para- or ortho-acylated naphthalenes (3 or 4) in good to high yields. The regioselectivity can be controlled by the ligand of a palladium catalyst. A sterically bulky ligand, ᵗBuPPh₂, affords para-acylated products 3, whereas a sterically less bulky ligand, Me₂PPh, provides ortho-acylat ...
- DOI:
- 10.1021/acs.joc.8b02343
-
http://dx.doi.org/10.1021/acs.joc.8b02343
- Author:
- Kato, Shuma; Suzuki, Yuko; Suzuki, Kota; Haraguchi, Ryosuke; Fukuzawa, Shin-ichi
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13965-13972
- ISSN:
- 1520-6904
- Subject:
- chemical structure; cycloaddition reactions; enantioselectivity; esters; organic chemistry
- Abstract:
- ... The AgOAc/ThioClickFerrophos complex catalyzed conjugate additions and 1,3-dipolar cycloadditions of 3-methyl-4-nitro-5-styrylisoxazoles with 1-pyrroline-5-carboxylates and glycine imino esters to give the corresponding Michael adducts and cycloadducts, respectively, in good yields with excellent diastereo- and enantioselectivities. These reactions can provide pyrroline- or pyrrolidine-containing ...
- DOI:
- 10.1021/acs.joc.8b02309
-
http://dx.doi.org/10.1021/acs.joc.8b02309
- Author:
- Friedrich, Ryan M.; Sreenilayam, Gopeekrishnan; Hackbarth, Jacob; Friestad, Gregory K.
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13636-13649
- ISSN:
- 1520-6904
- Subject:
- alcohols; aldehydes; bioactive properties; catalytic activity; enantiomers; enantioselectivity; hydrolysis; organic chemistry; stereochemistry
- Abstract:
- ... Diverse classes of natural products contain chiral 1,5-polyols, within which may be stereochemical triads of 1,5,9- and 1,5,7-triols. Biological activities associated with compounds containing these motifs warrant targeted synthetic strategies to access all stereoisomers of a 1,5-polyol family from cheap and easily accessible reagents while avoiding the need to determine configurations at each alc ...
- DOI:
- 10.1021/acs.joc.8b02033
-
http://dx.doi.org/10.1021/acs.joc.8b02033
- Author:
- Asahara, Haruyasu; Sofue, Ayano; Kuroda, Yasuyuki; Nishiwaki, Nagatoshi
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13691-13699
- ISSN:
- 1520-6904
- Subject:
- Grignard reagents; alcohols; alkenes; chemical bonding; chemical reactions; lithium; moieties; nitro compounds; nitrous acid; organic chemistry; potassium cyanide; triethylamine
- Abstract:
- ... In the work being reported here, β-nitrostyrenes bearing an ethoxycarbonyl group at the β-position serve as scaffolds for the synthesis of α,β-difunctionalized alkenes. Nitrocinnamates undergo Michael addition reactions with versatile sp³- and sp²-nucleophiles such as alcohols, Grignard reagents, alkylcopper, and dialkylzinc to afford β-substituted nitroethane derivatives. However, various attempt ...
- DOI:
- 10.1021/acs.joc.8b01865
-
http://dx.doi.org/10.1021/acs.joc.8b01865
- Author:
- Dinda, Shrabani
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 13911-13921
- ISSN:
- 1520-6904
- Subject:
- aldehydes; allylation; ascorbic acid; carbon; catalysts; chemical bonding; enantioselectivity; hydrogen; ligands; mechanics; moieties; optical isomerism; organic chemistry; oxygen; platinum; prediction; screening
- Abstract:
- ... Computational investigations on the enantioselectivity observed in the allylation of cinnamaldehyde have been carried out using four closely related chiral platinum catalysts with ascorbic acid-based bisphosphinite ligands. Enantioselectivity depends on the substitution of hydrogen on the hydroxyl group by benzyl group(s) in the ascorbic acid framework. The key intermediate is assumed to be one, w ...
- DOI:
- 10.1021/acs.joc.8b02230
-
http://dx.doi.org/10.1021/acs.joc.8b02230
- Author:
- Shylaja, Adaikalam; Roja, Somi Santharam; Priya, Rakkappan Vishnu; Kumar, Raju Ranjith
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14084-14090
- ISSN:
- 1520-6904
- Subject:
- chemical reactions; chemical structure; dimethyl sulfoxide; fluorescence; iron; metal ions; organic chemistry
- Abstract:
- ... The synthesis of novel pyrazolo[3,4-h]quinoline-3-carbonitriles has been achieved through a one-pot, four-component domino strategy under solvent-free microwave conditions. One of these compounds exhibited fluorescence under UV lamp and was found to be highly sensitive toward Fe³⁺ ions in DMSO against various metal ions with a detection limit of 8.6 × 10–⁷ M. ...
- DOI:
- 10.1021/acs.joc.8b01991
-
http://dx.doi.org/10.1021/acs.joc.8b01991
- Author:
- Wu, Xin-Xing; Liu, Anjia; Mou, Mou; Chen, Hengfan; Chen, Shufeng
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14181-14194
- ISSN:
- 1520-6904
- Subject:
- catalytic activity; chemical reactions; chemical structure; organic chemistry; palladium; phenol
- Abstract:
- ... A novel palladium-catalyzed cascade carbopalladation/phenol dearomatization reaction has been achieved. The process provides a variety of indolone-, dihydrobenzofuran-, dihydrobenzopyran- and hydroquinoline-containing spirofused molecules bearing two quaternary centers in moderate to good yields. The potential synthetic utility of this method is demonstrated by a gram-scale experiment and further ...
- DOI:
- 10.1021/acs.joc.8b02363
-
http://dx.doi.org/10.1021/acs.joc.8b02363
- Author:
- Ramanathan, Mani; Liu, Shiuh-Tzung
- Source:
- Journal of organic chemistry 2018 v.83 no.22 pp. 14138-14145
- ISSN:
- 1520-6904
- Subject:
- amination; chemical bonding; chemical structure; cyclization reactions; nitriles; organic chemistry; salts; synthesis
- Abstract:
- ... A one-pot synthesis of quinazolino[3,4-a]quinazolin-13-ones was realized from the direct reaction of o-(methoxycarbonyl)benzenediazonium salts, nitriles, and 2-cyanoanilines in moderate to good yields. This method utilizes the in situ generation of reactive N-arylnitrilium ion, which undergoes further amination/tandem cyclization/amidation to deliver the desired polycyclic scaffolds with consecuti ...
- DOI:
- 10.1021/acs.joc.8b02239
-
http://dx.doi.org/10.1021/acs.joc.8b02239