Sequential Sonogashira and Suzuki Cross‐Coupling Reactions in the Indole and Indazole Series.
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Abstract For Abstract see ChemInform Abstract in Full Text.Keywords:
Indazole
Sonogashira coupling
Coupling reaction
Suzuki reaction
A specially optimized air-stable Pd on activated carbon catalyst is demonstrated to be a highly active (TON up to 36,000), selective and convenient heterogeneous catalyst for CC couplings of aryl halides in Heck, Suzuki, and Sonogashira reactions. The Pd/C catalyst developed allows extremely low Pd concentrations (down to 0.0025 mol% for Heck coupling, 0.005 mol% for Suzuki coupling) and high conversions of aryl bromides within a few hours. Easy and complete Pd separation and recovery is possible.
Sonogashira coupling
Heck Reaction
Suzuki reaction
Palladium catalyst
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3-Iodoindoles, 5-bromo-3-iodoindoles and 5-bromo-3-iodoindazoles have been studied with respect to their reactivity and selectivity in palladium catalyzed Sonogashira and Suzuki cross-coupling reactions. As a result, sequential Sonogashira-Sonogashira, Sonogashira-Suzuki, and Suzuki-Sonogashira reactions with 5-bromo-3-iodoindoles or indazoles were used to obtain a large range of new functionalized indoles and indazoles, which are potential 5-HT receptor ligands.
Sonogashira coupling
Indazole
Suzuki reaction
Coupling reaction
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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.
Sonogashira coupling
Coupling reaction
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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.
Sonogashira coupling
Isoxazole
Coupling reaction
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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.
Stille reaction
Sonogashira coupling
Coupling reaction
Organic Synthesis
Organic reaction
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A novel sequence of Sonogashira coupling and electrophilic addition to an ynone, with concomitant deprotection and cyclocondensation, opens a new one-pot synthesis of 3-halofurans; the method can be readily elaborated to a new sequential Sonogashira–addition–cyclocondensation–Suzuki reaction to furnish 2,3,5-trisubstituted furans in a one-pot fashion.
Sonogashira coupling
Suzuki reaction
One-pot synthesis
Sequence (biology)
Component (thermodynamics)
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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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Coupling reaction
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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.
Sonogashira coupling
Coupling reaction
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A facile synthesis of novel 7-alkynylindazole derivatives involving the Pd/C–PPh 3 –CuI catalysed Sonogashira coupling of 7-iodoindazole with a wide range of terminal alkynes in aqueous medium is reported. An X-ray crystallographic study established the molecular structure of 7-(pent-1-ynyl)-1 H-indazole.
Indazole
Sonogashira coupling
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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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Coupling reaction
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