Gold-catalyzed cyclization of 1-(2′-azidoaryl) propynols: synthesis of polysubstituted 4-quinolones

2019 ◽  
Vol 55 (98) ◽  
pp. 14769-14772 ◽  
Author(s):  
Xiang Wu ◽  
Lang-Lang Zheng ◽  
Li-Ping Zhao ◽  
Cheng-Feng Zhu ◽  
You-Gui Li
Keyword(s):  
Functional Groups ◽  
Mild Conditions ◽  
Carbon Migration ◽  
Reaction Works

α-Imino gold carbene intermediate is produced from 1-(2′-azidoaryl) propynols, which triggers a 1,2-carbon migration and is converted to 2,3-disubstituted 4-quinolones. The reaction works under mild conditions and tolerates various functional groups.

Borates as a Traceless Activation Group for Intermolecular Alkylarylation of Ethylene through Photoredox/Nickel Dual Catalysis

Synlett ◽  
2020 ◽  
Author(s):  
Shengqing Zhu ◽  
Lingling Chu ◽  
Xiaoliang Feng ◽  
Lei Guo
Keyword(s):  
Functional Groups ◽  
Aryl Halides ◽  
Nickel Catalysis ◽  
Mild Conditions ◽  
Dual Catalysis

AbstractA formal ethylene alkylarylation reaction with aryl halides and alkyl oxalates enabled by synergistic photoredox/nickel catalysis is reported. This protocol takes advantage of borates as a traceless activation group, achieving the formal ethylene difunctionalized products via a catalytic three-component 1,2-alkylarylation of vinyl borate followed by a base-assisted deborylation process. The mild conditions allow for excellent functional groups compatibility and broad substrate scope.

Consecutive Multicomponent Reactions: Synthesis of 3-Acyl-4-alkynyl-Substituted 1,3-Thiazolidines

Synthesis ◽  
2018 ◽  
Vol 50 (05) ◽  
pp. 1123-1132 ◽  
Author(s):  
Jürgen Martens ◽  
Torben Schlüter ◽  
Nils Frerichs ◽  
Marc Schmidtmann
Keyword(s):  
Functional Groups ◽  
Multicomponent Reactions ◽  
Terminal Alkynes ◽  
Synthetic Route ◽  
Acyl Chlorides ◽  
Mild Conditions ◽  
Three Component Reaction

This work describes the synthesis of compounds containing thiazolidine and propargylamidic motifs. Their preparation follows a synthetic route containing two multicomponent reactions. First, the Asinger four-component reaction is used to prepare 3-thiazolines and 3-oxazolines. Secondly, these heterocyclic imines are converted into propargylamides by a copper-catalyzed three-component reaction using acyl chlorides and terminal alkynes. The synthetic route is characterized by mild conditions and many functional groups are tolerated. The formation of an unexpected α-alkynoxyamide is also presented.

Efficient Synthesis of 3,4-Disubstituted 7-Azaindoles Employing SEM as a Dual Protecting–Activating Group

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2273-2278 ◽  
Author(s):  
Piroska Gyárfás ◽  
János Gerencsér ◽  
Warren S. Wade ◽  
László Ürögdi ◽  
Zoltán Novák ◽  
...  
Keyword(s):  
Functional Groups ◽  
Efficient Method ◽  
Reaction Times ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Efficient Synthesis ◽  
Mild Conditions

An efficient method for nucleophilic aromatic substitution on 7-azaindoles has been developed. The reaction is facilitated by the unique dual influence of SEM as both protecting and activating group, permitting mild conditions and short reaction times that are compatible with sensitive functional groups. The method is suitable for the synthesis of a broad range of products, most notably ethers.

Green synthesis of Opuntia-derived carbon nanodots for the catalytic decolourization of cationic dyes

2020 ◽  
Vol 44 (46) ◽  
pp. 20001-20012
Author(s):  
Sabrina A. Beker ◽  
Adam Truskewycz ◽  
Ivan Cole ◽  
Andrew S. Ball
Keyword(s):  
Green Synthesis ◽  
Functional Groups ◽  
Cationic Dyes ◽  
Carbon Nanodots ◽  
Mild Conditions

Carbon nanodots, rich in functional groups and synthesised using green precursors, catalyse the decolourization of dyes under mild conditions.

Cerium(IV) Tetrabutylammonium Nitrate (CTAN): A Mild and Efficient N-dearylation Agent for Synthesis of N-unsubstituted 2-azetidinones

2017 ◽  
Vol 41 (4) ◽  
pp. 246-249 ◽  
Author(s):  
Maaroof Zarei
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Mild Conditions ◽  
Tetrabutylammonium Nitrate

A simple and efficient protocol for the conversion of N-p-methoxyphenyl, N-p-ethoxyphenyl, N-p-methoxynaphthyl, N-3,4-dimethoxybenzyl and N-p-methoxybenzyl-2-azetidinones to N-unsubstituted 2-azetidinones using cerium(IV) tetrabutylammonium nitrate (CTAN) in dichloromethane is described. The method is compatible with a number of functional groups, and N-unsubstituted 2-azetidinones can be prepared under mild conditions at room temperature. The reaction is rapid, and pure products are obtained in good yields.

scholarly journals Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

2018 ◽  
Vol 14 ◽  
pp. 1946-1955 ◽  
Author(s):  
Takao Shoji ◽  
Hiroki Fukutomi ◽  
Yohei Okada ◽  
Kazuhiro Chiba
Keyword(s):  
Functional Groups ◽  
Phosphodiester Bond ◽  
Mild Conditions ◽  
Naturally Occurring

Artificial orthogonal bond formations such as the alkyne–azide cycloaddition have enabled selective bioconjugations under mild conditions, yet naturally occurring linkages between native functional groups would be more straightforward to elaborate bioconjugates. Herein, we describe the use of a phosphodiester bond as a versatile option to access various bioconjugates. An opposite activation strategy, involving 5’-phosphitylation of the supported oligonucleotides, has allowed several biomolecules that possess an unactivated alcohol to be directly conjugated. It should be noted that there is no need to pre-install artificial functional groups and undesired and unpredictable perturbations possibly caused by bioconjugation can be minimized.

scholarly journals Directed Markovnikov Hydroarylation and Hydroalkenylation of Alkenes Under Nickel Catalysis

2021 ◽  
Author(s):  
Zi-Qi Li ◽  
Omar Apolinar ◽  
Ruohan Deng ◽  
Keary Engle
Keyword(s):  
Functional Groups ◽  
Product Yield ◽  
Computational Studies ◽  
Nickel Catalysis ◽  
Reaction Conditions ◽  
Full Account ◽  
Coordination Properties ◽  
Mild Conditions ◽  
Limiting Step ◽  
Shed Light

We report a full account of our research on nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of non-conjugated alkenes, which has yielded a toolkit of methods that proceed under mild conditions with alkenyl sulfonamide, ketone, and amide substrates. Regioselectivity is controlled through catalyst coordination to the native Lewis basic functional groups contained within these substrates. To maximize product yield, reaction conditions were fine-tuned for each substrate class, reflecting the different coordination properties of the directing functionality. Detailed kinetic and computational studies shed light on the mechanism of this family of transformations, pointing to transmetalation as the turnover-limiting step.

Photoredox-catalyzed sulfonylation of alkyl iodides, sulfur dioxide, and electron-deficient alkenes

2019 ◽  
Vol 55 (15) ◽  
pp. 2214-2217 ◽  
Author(s):  
Shengqing Ye ◽  
Danqing Zheng ◽  
Jie Wu ◽  
Guanyinsheng Qiu
Keyword(s):  
Sulfur Dioxide ◽  
Functional Groups ◽  
Mild Conditions ◽  
Alkyl Iodides

A photoredox-catalyzed sulfonylation of alkyl iodides, sulfur dioxide, and electron-deficient alkenes under mild conditions is achieved. Various functional groups including nitro, halo, acetyl, sufonyl, and pyridinyl are all tolerated under the photoredox conditions.

Ligand-Free and Solvent-Free Synthesis of 1,3-Disubstituted Naphthalenes through Stille Coupling

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 903-906
Author(s):  
Taoufik Rohand ◽  
Sanae Sbi ◽  
Victor Mkpenie ◽  
Kiyoshi Tanemura
Keyword(s):  
Functional Groups ◽  
Acetyl Chloride ◽  
Stille Coupling ◽  
Mechanistic Studies ◽  
Major Step ◽  
Mild Conditions ◽  
Synthetic Strategy ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Solvent Free Synthesis

A variety of 1,3-disubstituted naphthalenes have been prepared by palladium-catalyzed annulation of (o-ethynylphenyl)acetyl chloride with design of a new synthetic strategy by Stille coupling using functionalized organostannanes. The method affords excellent yields of the substituted naphthalenes and accommodates a wide variety of functional groups under mild conditions. Mechanistic studies show intramolecular cyclization as a major step following C–C bond coupling.

Cobalt-Catalyzed Oxidative [4+2] Annulation of Benzamides with Dihydrofuran: A Facile Route to Tetrahydrofuro[2,3-c]isoquinolinone

Synthesis ◽  
2021 ◽  
Author(s):  
Zhuo Zhuo Zhang ◽  
Gang Zhou ◽  
Fan-Rui Huang ◽  
Bing-Feng Shi
Keyword(s):  
Functional Groups ◽  
Efficient Catalyst ◽  
Mild Conditions ◽  
Facile Route

A cobalt-catalyzed oxidative [4 + 2] annulation of benzamides with dihydrofuran was developed for the expeditious synthesis of terahydrofuro[2,3-c]isoquinolinone. Commercially available and inexpensive Co(OAc)2∙4H2O was used as an efficient catalyst. Various functional groups were tolerated, affording the desired products in good yields with excellent regioselectivity and good diastereoselectivity under mild conditions.

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