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You searched for: Journal Journal of organic chemistry Remove constraint Journal: Journal of organic chemistry Publication Year 2018 Remove constraint Publication Year: 2018 Source 2018 v.83 no.22 Remove constraint Source: 2018 v.83 no.22
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1. Regiocontrolled Halogen Dance of Bromothiophenes and Bromofurans

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

2. Ag-Mediated Trifluoromethylthiolation of Inert Csp³–H Bond

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

3. Bisulfate Salt-Catalyzed Friedel–Crafts Benzylation of Arenes with Benzylic Alcohols

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

4. Stereoselective Synthesis of the ABC Ring System of Aspterpenacids

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

5. Synthesis of 5-Aryl-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts

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

6. One-Pot Synthesis of Dibenzo[b,d]oxepines via Olefinic C–F Bond Functionalization and Intramolecular Pd-Catalyzed C–H Arylation

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

7. Nickel-Catalyzed Benzylation of Aryl Alkenes with Benzylamines via C–N Bond Activation

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

8. Substrate-Controlled Domino Reactions of Crotonate-Derived Sulfur Ylides: Synthesis of Benzothiophene Derivatives

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

9. Synthesis of Benzoindolizines through 1,5-Electrocyclization/Oxidation Cascades

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

10. Unified Strategy for 1,5,9- and 1,5,7-Triols via Configuration-Encoded 1,5-Polyol Synthesis: Preparation and Coupling of C15–C25 and C26–C40 Fragments of Tetrafibricin

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

11. Circularly Polarized Luminescence of Boronic Acid-Derived Salicylidenehydrazone Complexes Containing Chiral Boron as Stereogenic Unit

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

12. Diastereospecific and Highly Site-Selective Functionalization of C₇₀ Fullerene by a Reaction with Diethyl N-Arylaziridine-2,3-dicarboxylates

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

13. Palladium-Catalyzed Ligand-Controlled Regioselective Nucleophilic Aromatic Substitution of 1-(Chloromethyl)naphthalenes with Arylacetonitriles

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

14. Silver-Catalyzed Diastereo- and Enantioselective Michael Addition and 1,3-Dipolar Cycloaddition Reactions of Imino Esters to 3-Methyl-4-nitro-5-styrylisoxazoles

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

15. Unified Strategy for 1,5,9- and 1,5,7-Triols via Configuration-Encoded 1,5-Polyol Synthesis: Enantioselective Preparation of γ-Sulfonyl-α-silyloxyaldehydes and Iterative Julia–Kocienski Coupling

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

16. Alkynylation and Cyanation of Alkenes Using Diverse Properties of a Nitro Group

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

17. Computational Study of Enantioselectivity in the Asymmetric Allylation of Aldehydes with Chiral Pt(II) Phosphinite Complexes

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

18. Four-Component Domino Synthesis of Pyrazolo[3,4-h]quinoline-3-carbonitriles: “Turn-Off” Fluorescent Chemosensor for Fe³⁺ Ions

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

19. Palladium-Catalyzed Cascade Carbopalladation/Phenol Dearomatization Reaction: Construction of Diversely Functionalized Spirocarbocyclic Scaffolds

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

20. Preparation of Quinazolinoquinazolinones via a Cascade Approach

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