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Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 40, 2009 - Issue 2

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Nickel-Catalyzed Alkynylation of Aryl Iodides (Sonogashira Reaction) in Water

Mohammad Bakherad Faculty of Chemistry, Shahrood University of Technology, Shahrood, IranCorrespondence[email protected]

Ali Keivanloo Faculty of Chemistry, Shahrood University of Technology, Shahrood, Iran

Samira Mihanparast Faculty of Chemistry, Shahrood University of Technology, Shahrood, Iran

Pages 179-185 | Received 25 Aug 2008, Published online: 29 Dec 2009

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https://doi.org/10.1080/00397910802630187

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Elena Braconi, Edouard Godineau, Tomas Smejkal & Simon Jäckh. (2024) Nickel‐Catalyzed Sonogashira Couplings: Extending the Reaction Scope to Aryl Bromides and Chlorides. Advanced Synthesis & Catalysis 366:7, pages 1551-1558.
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Mohammad Javaherian & Parviz Movaheditabar. (2023) On-water biphasic organic synthesis. Journal of the Iranian Chemical Society 20:9, pages 2103-2125.
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Yury N. Kotovshchikov, Artem A. Binyakovsky, Gennadij V. Latyshev, Nikolay V. Lukashev & Irina P. Beletskaya. (2022) Copper-catalyzed deacetonative Sonogashira coupling. Organic & Biomolecular Chemistry 20:38, pages 7650-7657.
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Nicholas E. Leadbeater. 2022. Comprehensive Organometallic Chemistry IV. Comprehensive Organometallic Chemistry IV 635 658 .

Dinesh Parshuram Satpute, Gargi Nikhil Vaidya, Shyam Kumar Lokhande, Sangita Dattatray Shinde, Shivkanya Madhavrao Bhujbal, Deep Rohan Chatterjee, Pooja Rana, Ashwini Venkatesh, Mithilesh Nagpure & Dinesh Kumar. (2021) Organic reactions in aqueous media catalyzed by nickel. Green Chemistry 23:17, pages 6273-6300.
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Sara S. E. Ghodsinia, Batool Akhlaghinia & Roya Jahanshahi. (2021) Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction in solvent-free conditions. Research on Chemical Intermediates 47:8, pages 3217-3244.
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Pravya P. Nair, Rose Mary Philip & Gopinathan Anilkumar. (2021) Nickel catalysts in Sonogashira coupling reactions. Organic & Biomolecular Chemistry 19:19, pages 4228-4242.
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Marzieh Daryanavard, Ali Ataei, Ezzat Rafiee & Mohammad Joshaghani. (2020) Ni(acac)2/2,6-bis(diphenylphosphino)pyridine/CuI: A highly efficient palladium-free homogeneous catalyst for the Sonogashira cross-coupling reaction. Inorganic Chemistry Communications 122, pages 108274.
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Felipe López-Saucedo, Alejandro Ramos-Ballesteros & Emilio Bucio. 2020. Green Sustainable Process for Chemical and Environmental Engineering and Science. Green Sustainable Process for Chemical and Environmental Engineering and Science 357 386 .

Anindita Dewan, Manashi Sarmah, Ashim J. Thakur, Pankaj Bharali & Utpal Bora. (2018) Greener Biogenic Approach for the Synthesis of Palladium Nanoparticles Using Papaya Peel: An Eco-Friendly Catalyst for C–C Coupling Reaction. ACS Omega 3:5, pages 5327-5335.
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Richard C. LarockRichard C. Larock & Li Zhang. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 56 .

Suresh Poudapally, Venkateshwarlu Gurram, Ramesh Garlapati, Chiranjeevi Tulluri, Uma Addepally, K. Vidya, Somesh Sharma, Subhabrata Sen & Narender Pottabathini. (2017) Cu‐free Sonogashira Type Cross‐Coupling of 6‐Halo‐2‐cyclopropyl‐3‐(pyridyl‐3‐ylmethyl) Quinazolin‐4(3 H )‐ones as Potential Antimicrobial Agents . Journal of Heterocyclic Chemistry 54:4, pages 2272-2286.
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Hideo Oka, Katsuya Kitai, Takeyuki Suzuki & Yasushi Obora. (2017) N,N-Dimethylformamide-stabilized copper nanoparticles as a catalyst precursor for Sonogashira–Hagihara cross coupling. RSC Advances 7:37, pages 22869-22874.
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Amrutha P. Thankachan, Thoppilan G. Abi, Kallikkakam S. Sindhu & Gopinathan Anilkumar . (2016) Experimental and Mechanistic Exploration of Zn‐Catalyzed Sonogashira–type Cross‐Coupling Reactions. ChemistrySelect 1:13, pages 3405-3412.
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Anette Petuker, Christian Merten & Ulf‐Peter Apfel. (2015) Modulating Sonogashira Cross‐Coupling Reactivity in Four‐Coordinate Nickel Complexes by Using Geometric Control. European Journal of Inorganic Chemistry 2015:12, pages 2139-2144.
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Firouz Matloubi Moghaddam, Ghazal Tavakoli & Hamid Reza Rezvani. (2015) A copper-free Sonogashira reaction using nickel ferrite as catalyst in water. Catalysis Communications 60, pages 82-87.
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Najrul Hussain, Pranjal Gogoi, Puja Khare & Manash R. Das. (2015) Nickel nanoparticles supported on reduced graphene oxide sheets: a phosphine free, magnetically recoverable and cost effective catalyst for Sonogashira cross-coupling reactions. RSC Advances 5:125, pages 103105-103115.
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Gina M. Roberts, Wenya Lu & L. Keith Woo. (2015) Aqueous Sonogashira coupling of aryl halides with 1-alkynes under mild conditions: use of surfactants in cross-coupling reactions. RSC Advances 5:24, pages 18960-18971.
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Fatemeh Farjadian & Bahman Tamami. (2014) Poly(vinylpyridine)‐Grafted Silica Containing Palladium or Nickel Nanoparticles as Heterogeneous Catalysts for the Sonogashira Coupling Reaction. ChemPlusChem 79:12, pages 1767-1773.
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Rafael Chinchilla & Carmen Nájera. 2014. Modern Alkyne Chemistry. Modern Alkyne Chemistry 269 298 .

Mohsen Esmaeilpour, Jaber Javidi, Fatemeh Nowroozi Dodeji & Mehdi Mokhtari Abarghoui. (2014) M(II) Schiff base complexes (M = zinc, manganese, cadmium, cobalt, copper, nickel, iron, and palladium) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: synthesis, characterization and catalytic activity for Sonogashira–Hagihara coupling reactions. Transition Metal Chemistry 39:7, pages 797-809.
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Esmaeilpour Mohsen, Javidi Jaber, Mokhtari Abarghoui Mehdi & Nowroozi Dodeji Fatemeh. (2013) Synthesis and characterization of Fe3O4@SiO2–polymer-imid–Pd magnetic porous nanospheres and their application as a novel recyclable catalyst for Sonogashira–Hagihara coupling reactions. Journal of the Iranian Chemical Society 11:2, pages 499-510.
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Mohammad Bakherad. (2013) Recent progress and current applications of Sonogashira coupling reaction in water. Applied Organometallic Chemistry 27:3, pages 125-140.
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Kevin H. Shaughnessy. 2013. Metal‐Catalyzed Reactions in Water. Metal‐Catalyzed Reactions in Water 1 46 .

Ruiping Wang, Song Mo, Yongzhong Lu & Zengming Shen. (2011) Domino Sonogashira Coupling/Cyclization Reaction Catalyzed by Copper and ppb Levels of Palladium: A Concise Route to Indoles and Benzo[ b ]furans . Advanced Synthesis & Catalysis 353:5, pages 713-718.
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Daniel Rosario-Amorin, Manuel Gaboyard, Rodolphe Clérac, Sylvain Nlate & Karine Heuzé. (2011) Enhanced catalyst recovery in an aqueous copper-free Sonogashira cross-coupling reaction. Dalton Trans. 40:1, pages 44-46.
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Mohammad Bakherad, Ali Keivanloo & Samira Mihanparast. (2010) ChemInform Abstract: Nickel‐Catalyzed Alkynylation of Aryl Iodides (Sonogashira Reaction) in Water.. ChemInform 41:25.
Crossref

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Nickel-Catalyzed Alkynylation of Aryl Iodides (Sonogashira Reaction) in Water

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