scholarly journals Cross-dehydrogenative coupling for the intermolecular C–O bond formation

2015 ◽  
Vol 11 ◽  
pp. 92-146 ◽  
Author(s):  
Igor B Krylov ◽  
Vera A Vil’ ◽  
Alexander O Terent’ev
Keyword(s):  
Bond Formation ◽  
Coupling Reaction ◽  
Present Review ◽  
Published Data ◽  
Coupling Reactions ◽  
Sulfonic Acids ◽  
Dehydrogenative Coupling ◽  
Starting Compound ◽  
The Cross

The present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O2CR)2 reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.).

scholarly journals Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (20) ◽  
pp. 4586-4598 ◽  
Author(s):  
Martyn Henry ◽  
Mohamed Mostafa ◽  
Andrew Sutherland
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Dehydrogenative Coupling ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.1 Introduction2 Intramolecular C–N Cross-Dehydrogenative Coupling2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation3 Intermolecular C–N Cross-Dehydrogenative Coupling3.1 ortho-C–N Bond Formation3.1.1 Copper-Catalyzed Reactions3.1.2 Other Transition-Metal-Catalyzed Reactions3.2 meta- and para-C–N Bond Formation4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds5 Conclusions

scholarly journals Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities

RSC Advances ◽  
2018 ◽  
Vol 8 (70) ◽  
pp. 40000-40015 ◽  
Author(s):  
Nedra Touj ◽  
Abdullah S. Al-Ayed ◽  
Mathieu Sauthier ◽  
Lamjed Mansour ◽  
Abdel Halim Harrath ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Cytotoxic Activities ◽  
Coupling Reactions ◽  
Component System ◽  
Arylboronic Acids ◽  
Cross Coupling Reaction

The in situ prepared four component system Pd(OAc)2, 1,3-dialkylbenzimidazolium halides 2a–i and 4a–i, K2CO3 under CO atmosphere catalyses carbonylative cross-coupling reaction of 2-bromopyridine with various boronic acids to yield unsymmetrical arylpyridine ketones.

An easily prepared palladium-hydrogel nanocomposite catalyst for C–C coupling reactions

2014 ◽  
Vol 2 (44) ◽  
pp. 18952-18958 ◽  
Author(s):  
Mitasree Maity ◽  
Uday Maitra
Keyword(s):  
Palladium Nanoparticles ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Sodium Cyanoborohydride ◽  
Efficient Catalyst ◽  
Suzuki Coupling Reaction ◽  
Reaction In Water ◽  
Hydrogel Nanocomposite

Palladium nanoparticles were efficiently prepared in situ by sodium cyanoborohydride reduction of Pd(ii) at room temperature using calcium-cholate hydrogel fibers as templates. The PdNPs self-organize on the gel fibers, which supports the controlled growth as well as stabilization of PdNPs. The hybrid xerogel was used as an efficient catalyst for the Suzuki coupling reaction in water.

scholarly journals Thiol–ene coupling reaction achievement and monitoring by “in situ” UV irradiation NMR spectroscopy

RSC Advances ◽  
2020 ◽  
Vol 10 (42) ◽  
pp. 25214-25222
Author(s):  
Natalia Toncheva-Moncheva ◽  
Miroslav Dangalov ◽  
Nikolay G. Vassilev ◽  
Christo P. Novakov
Keyword(s):  
Nmr Spectroscopy ◽  
Uv Irradiation ◽  
Glycidyl Ether ◽  
Coupling Reaction ◽  
Polyethylene Glycols ◽  
Coupling Reactions ◽  
Uv Illumination ◽  
Allyl Glycidyl Ether

An “In situ” LED UV illumination NMR setup for achievement of initiator-free coupling reactions of allyl-functionalized poly(allyl glycidyl ether) with polyethylene glycols thiols.

scholarly journals Enantioselective Iron/Bisquinolyldiamine Ligand-Catalyzed Oxidative Coupling Reaction of 2-Naphthols

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 852 ◽  
Author(s):  
Lin-Yang Wu ◽  
Muhammad Usman ◽  
Wen-Bo Liu
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Iron Complex ◽  
Coupling Reactions ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

An iron-catalyzed asymmetric oxidative homo-coupling of 2-naphthols for the synthesis of 1,1′-Bi-2-naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron-complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)-N1,N2-di(quinolin-8-yl)cyclohexane-1,2-diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.

scholarly journals Palladium-catalyzed Suzuki-Miyaura coupling of thioureas or thioamides

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Shaoyu Mai ◽  
Wendong Li ◽  
Xue Li ◽  
Yingwei Zhao ◽  
Qiuling Song
Keyword(s):  
Silver Salt ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Mechanistic Studies ◽  
Aromatic Rings ◽  
Cross Coupling Reactions ◽  
Broad Array ◽  
Palladium Catalyzed

AbstractCross-coupling reactions involving metal carbene intermediates play an increasingly important role in C–C bond formation. Expanding the carbene precursors to a broader range of starting materials and more diverse products is an ongoing challenge in synthetic organic chemistry. Herein, we report a Suzuki-Miyaura coupling reaction of in situ-generated Pd–carbene complexes via desulfurization of thioureas or thioamides. This strategy enables the preparation of a broad array of substituted amidinium salts and unsymmetrical diaryl ketones. The reaction is readily scalable, compatible with bromo groups on aromatic rings, tolerant to moisture and air and has a broad substrate scope. Furthermore, a single crystal structure of Pd-diaminocarbene complex is obtained and proven to be the key intermediate in both catalytic and stoichiometric reactions. Preliminary mechanistic studies demonstrate the dual role of the silver salt as a desulfurating reagent assisting the elimination of sulfur and as oxidant facilitating the PdII/Pd0/PdII catalytic cycle.

scholarly journals Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2853-2866 ◽  
Author(s):  
Arkaitz Correa ◽  
Marcos Segundo
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Short Review ◽  
Great Promise ◽  
Coupling Reactions ◽  
Atom Economy ◽  
Bond Forming ◽  
Dehydrogenative Coupling ◽  
Peptide Derivatives

The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and peptide derivatives with a variety of nucleophilic coupling partners.1 Introduction2 C–C Bond-Forming Oxidative Couplings2.1 Reaction with Alkynes2.2 Reaction with Alkenes2.3 Reaction with (Hetero)arenes2.4 Reaction with Alkyl Reagents3 C–Heteroatom Bond-Forming Oxidative Couplings3.1 C–P Bond Formation3.2 C–N Bond Formation3.3 C–O and C–S Bond Formation4 Conclusions

In Situ Coloration of Silk with Coupling Reaction and the Spectrum Characteristics

2013 ◽  
Vol 796 ◽  
pp. 428-431
Author(s):  
Wei Guo Chen ◽  
Zong Qian Wang ◽  
Zhi Hua Cui ◽  
Zhao Cheng Meng
Keyword(s):  
Silk Fibroin ◽  
Coupling Reaction ◽  
Coupling Reactions ◽  
Tyrosine Residue ◽  
Fastness Properties ◽  
Silk Industry ◽  
Tyrosine Residues ◽  
Spectrum Characteristics ◽  
Dyeing Method

High wet fastness dyeing is always the hot issue of silk industry. The plenty of tyrosine residue in silk protein may contribute an opportunity to solve this problem. In this paper, in situ coloration of silk is described using coupling reaction between diazonium compounds, made from different arylamine derivatives, and tyrosine residues in the silk fibroin. The spectra of coloured silk and the washing and rubbing fastness were measured. The results suggest that the use of coupling reactions could be developed into a dyeing method for silk. The wet fastness properties of such coloration are good because the chromophores are incorporated into the protein chains.

Functionalized α,β-ynones: efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (111) ◽  
pp. 109296-109300 ◽  
Author(s):  
Xian Wang ◽  
Zhenhua Wang ◽  
Zunyuan Xie ◽  
Guofang Zhang ◽  
Weiqiang Zhang ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Cross Coupling Reactions ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
The Cross

1,3-Yones as σ-, π-electron donating ligands significantly accelerated the cross-coupling reactions of aryl iodides with terminal alkynes, in which as low as 0.1 to 1 mol% of CuI were efficiently activated.

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