Sequential Sonogashira and Glaser coupling reactions: facile access to 1,4-disubstituted 1,3-butadiynes from arylbromide
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Abstract One of the most straightforward methods for the synthesis of disubstituted alkynes is the transition metal catalyzed Sonogashira‐type cross‐coupling reactions. Herein we report a detailed study of our recent research on the first Zn‐catalyzed protocol for C(sp 2 )–C(sp) cross‐coupling reaction of aryl iodides with terminal alkynes. A wide range of functional groups were tolerated in the reaction and both functionally and structurally diverse diaryl acetylenes were prepared efficiently using this protocol. The reaction mechanism for the Zn‐catalyzed Sonogashira‐type coupling reaction was investigated by means of density functional theory (DFT) methods on a model system. The calculations were performed using hybrid Becke Perdew Functional (BPV86) in conjugation with LANL‐2DZ basis set and found that the reaction pathway involves oxidative addition and reductive elimination mechanism.
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Herein we report on the selective iron-catalyzed cross-coupling reaction of terminal phenylacetylenes with iodo-aryl derivatives to afford the respective coupling products in the presence of 10 mol% FeCl2(bdmd) and 10 mol% [Cu(CH3CN)4]BF4 (bdmd=bis((diphenylphosphanyl)methyl)diphenylsilane). The yields are moderate to good in 1,4-dioxane or DMF. This is the first example of a well-defined and fully analysed ferrous complex acting as a precatalyst in Sonogashira cross-coupling reactions. Notably, FeCl2(bdmd) is compatible with reactive substituents such as carbonyl-, carboxyl-, hydroxy-, and amino-groups, which allows for an effective cross-coupling reaction in the presence of such functional groups.
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A Pd-catalyzed Sonogashira cross-coupling reaction for the synthesis of C4-alkynylisoxazoles from 3,5-disubsitituted-4-iodoisoxazoles and terminal alkynes was described, which could afford the corresponding products with high yield (up to 98%). The results indicated that the steric effect from the group at the C3 position of the isoxazole had greater influence on the cross-coupling reaction than that from the group at the C5 position. In addition, the group at the C3 position of the isoxazole showed negligible electronic effects on the cross-coupling reaction. Furthermore, a gram-scale reaction of the Sonogashira coupling reaction was also investigated. Finally, a plausible mechanism for the Sonogashira coupling reaction was proposed.
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The review summarizes the use of metal nanoparticles as catalysts in cross-coupling reactions. Nanoparticle-sized catalysts are used in a variety of reactions, however, this chapter will focus on their use in the following cross-coupling reactions: Suzuki-Miyaura, Mizoroki-Heck, Sonogashira, Ullmann and Stille. Catalysts in nanoparticle size are often supported on other materials, referred to as catalyst supports. The various catalyst supports utilized for nanoparticles used in cross-coupling reactions will also be presented. Keywords: Nanoparticles, catalysis, palladium, copper, cross-coupling reactions, Suzuki-Miyaura reaction, Mizoroki-Heck reaction, Sonogashira reaction, Ullmann reaction, Stille reaction.
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Palladium nanoparticles were supported on a bed of Fe 3 O 4 @‐NH 2 @Murexide using a simple and efficient method, and characterized using Fourier transform infrared spectroscopy, X‐ray diffraction, scanning and transmission electron microscopies and inductively coupled plasma optical emission spectrometry. The catalytic system showed great efficiency in cross‐coupling reaction of aryl iodides and arylboronic acid and in Sonogashira cross‐coupling reaction in the green solvent EtOH–H 2 O (1:1). The isolation and recovery of the catalyst were simple and facile and it could be used for several successive Suzuki–Miyaura coupling and Sonogashira cross‐coupling reactions. Copyright © 2016 John Wiley & Sons, Ltd.
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The Sonogashira coupling reaction is not catalyzed by AuI/dppe in the absence of Pd complexes. However, addition of 0.1 mol % of Pd(0) led to efficient cross-coupling reactions. The most plausible catalytic cycles for the Au-catalyzed cross-coupling reactions have been examined and are unlikely in the absence of Pd contamination.
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Sonogashira cross coupling is a well-known reaction for the formation of carbon-carbon bond. It involves the coupling of aryl halides with terminal alkynes to synthesize versatile functionalized alkyne scaffolds having diverse applications. Many of the natural products and important pharmaceutical drugs can be obtained through this reaction. In this regard, hectic progress has been put by the synthetic chemists to make this cross coupling more effective. This review article discloses mild and environmental friendly reaction conditions of Sonogashira cross coupling developed during 2013-2018.
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In this paper, we report the successful synthesis of new 2-phenyl-3-substituted furo/thieno[2,3-b ]quinoxaline derivatives from 2-chloro-3-methoxyquinoxaline and 2-chloro-3-(methylthio)quinoxaline by a three-step approach.
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Abstract Sequential Suzuki and Sonogashira reactions afford the synthetically important target compounds in good to excellent yields.
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An alternative approach to develop a Pd catalyst based on dendrimer‐functionalized graphene oxide for C‐C cross‐coupling reactions is reported. Pd@MGO‐D‐NH 2 has been synthesized by incipient wet impregnation method. The structure of the catalyst was thoroughly characterized by a set of analytical techniques such as TEM, BET, SEM/EDS, FTIR, and elemental mapping analysis. Then, the catalytic activity of the catalyst was scrutinized for promoting sonogashira C‐C coupling reaction. The results manifested that Pd@MGO‐D‐NH 2 was able to catalyze the coupling reaction to obtain high coupling yields in short reaction time. The results of present work are hoped to aid the development of new class of heterogeneous catalysts as the high performance candidate for industrial applications.
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