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Journal ArticleDOI

Oxygen-Promoted Suzuki-Miyaura Reaction for Efficient Construction of Biaryls

Chun Liu, +1 more
- 01 Feb 2016 - 
- Vol. 16, Iss: 1, pp 84-97
TLDR
Interestingly, the oxygen-promoting effect has been observed in different reaction media, including polyethylene glycol, organic/water mixed solvents and pure water, which demonstrates high efficiency for the construction of biaryls.
Abstract
As one of the most powerful and versatile methods for the construction of carbon-carbon bonds, the Suzuki-Miyaura cross-coupling reaction has attracted great attention over the past three decades. In recent years, a huge amount of interest has been focused on the development of ligand-free Suzuki-Miyaura reaction systems, which have the advantages of low cost, mild reaction conditions, and easy operation. So far, a number of ligand-free Suzuki-Miyaura reaction systems have been developed by using simple palladium salts, nanopalladium, or supported palladium catalysts. In this account, we will review our recent research on the oxygen-promoted ligand-free Suzuki-Miyaura reaction. Interestingly, the oxygen-promoting effect has been observed in different reaction media, including polyethylene glycol, organic/water mixed solvents and pure water. The oxygen-promoted reaction systems demonstrate high efficiency for the construction of biaryls.

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Citations
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Journal ArticleDOI

Synthesis of Biaryls via Ligand‐Free Suzuki–Miyaura Cross‐Coupling Reactions: A Review of Homogeneous and Heterogeneous Catalytic Developments

TL;DR: The literature reporting ligand-free synthesis of biaryls from 2010 to May 2015 has been reviewed in this paper, and the catalysts outlined here allow convenient and green synthetic pathways specifically for the construction of C-C bonds.
Journal ArticleDOI

Greener Biogenic Approach for the Synthesis of Palladium Nanoparticles Using Papaya Peel: An Eco-Friendly Catalyst for C-C Coupling Reaction.

TL;DR: Pd nanoparticles (Pd NPs) are synthesized using the extract of waste papaya peel without the assistance of any reducing agents, high-temperature calcination, and reduction procedures, and offer a simple and efficient methodology in direct Suzuki–Miyaura and Sonogashira coupling with excellent yields under mild reaction conditions.
Journal ArticleDOI

Late-Stage Diversification of Tryptophan-Derived Biomolecules

TL;DR: This Review primarily compiles the application of different cross‐coupling reactions to modify halotryptophan containing peptides or halogenated, biologically active compounds derived from tryptophan.
Journal ArticleDOI

Synthesis of Polyflourinated Biphenyls; Pushing the Boundaries of Suzuki–Miyaura Cross Coupling with Electron-Poor Substrates

TL;DR: A general strategy for the synthesis of a wide range of highly fluorinated biphenyls, scalable and versatile without the need for elaborate phosphine ligands or Pd-precatalysts is reported.
Journal ArticleDOI

An improved Suzuki–Miyaura cross-coupling reaction with the aid of in situ generated PdNPs: evidence for enhancing effect with biphasic system

TL;DR: In this article, an improved Suzuki-Miyaura cross-coupling in WERSA (Water Extract of Rice Straw Ash) was presented, where the use of alcoholic co-solvent dramatically enhances the yield and generates in situ PdNPs during the reaction.
References
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Journal ArticleDOI

Palladium-catalyzed cross-coupling reactions of organoboron compounds

Norio Miyaura, +1 more
- 01 Nov 1995 - 
TL;DR: In this paper, a cross-coupling reaction is proposed for coupling 1 -Alkenylboron Derivatives: Synthesis of Conjugated Dienes 6.
Journal ArticleDOI

N-heterocyclic carbenes: a new concept in organometallic catalysis.

TL;DR: N-Heterocyclic carbenes have become universal ligands in organometallic and inorganic coordination chemistry as mentioned in this paper, and they not only bind to any transition metal, be it in low or high oxidation states, but also to main group elements such as beryllium, sulfur, and iodine.
Journal ArticleDOI

Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998

TL;DR: The palladium-catalyzed cross-coupling reaction between organoboron compounds and organic halides or triflates provides a powerful and general methodology for the formation of carbon-carbon bonds as discussed by the authors.
Journal ArticleDOI

Palladium-Catalyzed Coupling Reactions of Aryl Chlorides

TL;DR: This review summarizes both the seminal early work and the exciting recent developments in the area of palladium-catalyzed couplings of aryl chlorides.
Journal ArticleDOI

Palladium-catalyzed cross-coupling reactions in total synthesis.

TL;DR: In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
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