A novel one-pot three-component synthesis of 3-halofurans and sequential Suzuki coupling
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Abstract:
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.Keywords:
Sonogashira coupling
Suzuki reaction
One-pot synthesis
Sequence (biology)
Component (thermodynamics)
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In the first part of the thesis palladium nanocatalyst has been attempted to synthesize 1-(1-benzyl-1H-indol-3-yl)-3-(trimethylsilyl)prop-2-yn-1-one through copper free Sonogashira reaction condition using 1H-indole-3-carbonyl chloride and ethynyltrimethylsilane in order to synthesize intermediate for the synthesis of biologically active meridianin. This intermediate once accomplished can be in priciple used in one-pot three component synthesis following the acyl Sonogashira reaction via the coupling-addition-cyclocondensation sequence. In the second part of the thesis palladium nanoparticles fixed on single walled carbon nanotubes has been synthesized which serve as an efficient and reusable solid support for copper free Sonogashira reaction for acyl chlorides with terminal acetylenes. A wide array of ynones are synthesized in high yields under mild reaction condition. This simple protocol of ynone preparation in high yield was further explored in the multicomponent synthesis of 2,4-disubstituted pyrimidines derivative in one-pot fashion. Disubstituted pyrimidines were obtained in good yields applying one-pot three component synthesis following an acyl Sonogashira coupling-addition-cyclocondensation sequence.
Sonogashira coupling
One-pot synthesis
Coupling reaction
Derivative (finance)
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Abstract Pyrimidin‐2‐yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross‐coupled with arylboronic acids and terminal alkynes by using Pd(OAc) 2 ‐catalyzed Suzuki and Sonogashira reactions. A wide array of C2‐functionalized pyrimidines have been prepared in good to excellent yields. 2‐Arylpyridines and 2‐(oct‐1‐ynyl)pyridine were also synthesized.
Sonogashira coupling
Suzuki reaction
Coupling reaction
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Sonogashira coupling
One-pot synthesis
Coupling reaction
Rose (mathematics)
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Sonogashira coupling
Heck Reaction
Suzuki reaction
Coupling reaction
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Citations (59)
Abstract Two silylated Pd–NHC complexes were immobilized on hybrid silicas by sol‐gel cocondensation with tetraethyl orthosilicate (TEOS) and performed well as recyclable catalysts towards the Heck, Suzuki, and Sonogashira coupling reactions. Remarkable conversion and recyclability were achieved in the Suzuki reaction with a challenging aryl chloride. No side products and no undesired homocoupling were observed in Suzuki or Heck reactions, which facilitates the final purification step for the cross‐coupling products. High turnover numbers and turnover frequencies were found for copper‐ and phosphane‐free Sonogashira reaction between p ‐bromoacetophenone and phenylacetylene.
Sonogashira coupling
Heck Reaction
Phenylacetylene
Suzuki reaction
Turnover number
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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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One-pot synthesis of symmetric 1,4-disubstituted 1,3-diynes from iodoarenes and propiolic acid via Sonogashira reaction followed by Pd-catalyzed decarboxylative homocoupling is developed in high yields. Also, this system allows the one-pot synthesis of unsymmetric 1,4-disubstituted 1,3-diynes by cross-coupling of two different 3-substituted propiolic acids.
Sonogashira coupling
Sequence (biology)
One-pot synthesis
Decarboxylation
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Citations (85)
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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Citations (80)
Based upon a consecutive one-pot Sonogashira-Glaser coupling-cyclization sequence a variety of 2,5-di(hetero)arylthiophenes were synthesized in moderate to good yields. A single Pd/Cu-catalyst system, without further catalyst addition, and easily available, stable starting materials were used, resulting in a concise and highly efficient route for the synthesis of the title compounds. This novel pseudo five-component synthesis starting from iodo(hetero)arenes is particularly suitable as a direct access to well-defined thiophene oligomers, which are of peculiar interest in materials science.
Sonogashira coupling
Sequence (biology)
Component (thermodynamics)
One-pot synthesis
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Hitherto unknown pentaalkynylpyridines have been prepared in high yields by Sonogashira cross-coupling reactions of pentachloropyridine. Their photophysical properties were studied and compared to those of penta- and hexaalkynylbenzenes which were efficiently prepared by the first Sonogashira reactions of pentachlorobenzene and hexachlorobenzene. The pentaalkynylpyridines show promising fluorescence properties because of their high quantum yields.
Sonogashira coupling
Hexachlorobenzene
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Citations (38)