Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol

Synlett ◽  
2019 ◽  
Vol 30 (19) ◽  
pp. 2161-2168
Author(s):  
Fangyu Du ◽  
Qifan Zhou ◽  
Yang Fu ◽  
Yuanguang Chen ◽  
Ying Wu ◽  
...  
Keyword(s):  
Diethylene Glycol ◽  
Functional Group ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Mild Conditions ◽  
Natural Ligand ◽  
Highly Effective ◽  
High Yields

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C–N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

2020 ◽  
Vol 17 (11) ◽  
pp. 857-863
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Phenylboronic Acid ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Salen Complex ◽  
Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3317-3330 ◽  
Author(s):  
Cédric Tresse ◽  
Stéphane Schweizer ◽  
Philippe Bisseret ◽  
Jacques Lalevée ◽  
Gwilherm Evano ◽  
...  
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.

Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1803-1808 ◽  
Author(s):  
Yan Zhang ◽  
Zhe-Yao Hu ◽  
Xin-Chang Li ◽  
Xun-Xiang Guo
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Aryl Halides ◽  
Synthetic Method ◽  
Alternative Route ◽  
Reaction Proceeds ◽  
High Yields

A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles in high yields. This synthetic method shows good functional group tolerance and offers an alternative route to construct N-aryl indoles.

scholarly journals Direct Sulfoxidation of Aromatic Methyl Thioethers with Aryl Halides by Copper-Catalyzed C(sp3)–H Bond Activation

Catalysts ◽  
2019 ◽  
Vol 9 (1) ◽  
pp. 105
Author(s):  
Runsheng Xu ◽  
Yueer Zhu ◽  
Feixiang Xiong ◽  
Suli Tong
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Aryl Halides ◽  
Biologically Active ◽  
Mild Conditions ◽  
Methyl Thioethers ◽  
High Yields

A copper-catalyzed direct sulfoxidation reaction by C(sp3)–H bond activation has been developed. Starting from sample aromatic methyl thioethers with aryl halides, versatile biologically-active arylbenzylsulfoxide derivatives were efficiently synthesized in good to high yields under mild conditions. This new methodology provides an economical approach toward C(sp3)–C(sp2) bond formation.

Iron(III)/TEMPO-Catalyzed Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles by Oxidative Cyclization under Mild Conditions

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1373-1377 ◽  
Author(s):  
Chengrong Ding ◽  
Guofu Zhang ◽  
Yidong Yu ◽  
Yiyong Zhao ◽  
Xiaoqiang Xie
Keyword(s):  
Functional Group ◽  
Oxidative Cyclization ◽  
Mild Conditions ◽  
Broad Scope ◽  
Oxadiazole Derivatives ◽  
High Yields

A simple and efficient cationic Fe(III)/TEMPO-catalyzed oxidative cyclization of aroyl hydrazones has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazole derivatives. The reaction offers a broad scope, good functional-group tolerance, and high yields under mild conditions in the presence of O2.

scholarly journals Synthesis of Stereodefined 1,1-Diborylalkenes via Copper-Catalyzed Diboration of Terminal Alkynes

2020 ◽  
Author(s):  
Yang Gao ◽  
Zhong-Qian Wu ◽  
Keary Engle
Keyword(s):  
Functional Group ◽  
Aryl Halides ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Tandem Process ◽  
Trisubstituted Alkenes

A copper-catalyzed method for the <i>E</i>-selective 1,1-diboration of terminal alkynes is described. The tandem process involves sequential dehydrogenative borylation of the alkyne substrate with HBdan (HBdan = 1,8-diaminonaphthalatoborane), followed by hydroboration with HBpin (HBpin = pinacolborane). This method proceeds efficiently under mild conditions, furnishing 1,1-diborylalkenes with excellent stereoselectivity and broad functional-group tolerance. Taking advantage of the different reactivities of the two boryl moieties, the products can then be employed in stepwise cross-couplings with aryl halides for the stereocontrolled construction of trisubstituted alkenes.

Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 319-324 ◽  
Author(s):  
Zhaozhan Wang ◽  
Tao Song ◽  
Yong Yang
Keyword(s):  
Functional Group ◽  
Direct Synthesis ◽  
Biologically Active ◽  
One Pot ◽  
Mild Conditions ◽  
Wide Range ◽  
High Yields

A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.

H2O as the Sole Hydrogen Source for Ni-Catalyzed Reduction of Alkenes

2019 ◽  
Author(s):  
Yichen Wu ◽  
Tao liu ◽  
Dongping Chen ◽  
Daoming Wang ◽  
Peng Wang
Keyword(s):  
Nickel Catalyst ◽  
Selective Hydrogenation ◽  
Functional Group ◽  
Catalytic Amount ◽  
Mild Conditions ◽  
Water As Solvent ◽  
Direct Hydrogenation ◽  
High Yields

Herein, we reported a nickel catalyzed hydrogenation of alkenes with water as the sole hydrogen source. Employing Zn as reductant and water as solvent in the presence of a catalytic amount of nickel catalyst led to direct hydrogenation of a series of electron-rich and electron-deficient alkenes in high yields. This protocol features unprecedented heterocycle and functional group tolerance under facile and mild conditions. Selective hydrogenation of the substrates containing additional reducible functionalities, such as alkenyl, alkynyl, chloride, ketone, and benzyl group etc, was also realized.

Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: use of surfactants in cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (24) ◽  
pp. 18960-18971 ◽  
Author(s):  
Gina M. Roberts ◽  
Wenya Lu ◽  
L. Keith Woo
Keyword(s):  
Aqueous Solutions ◽  
Organic Solvents ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Bromide ◽  
Sonogashira Coupling ◽  
Mild Conditions ◽  
Cross Coupling Reactions

Aqueous solutions of common and inexpensive surfactants (e.g. SDS and CTAB) are surveyed as an alternative to organic solvents in Sonogashira cross-coupling. Aryl-bromide substrates are best coupled under Cu-free conditions.

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