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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 2
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Original Articles

A Facile Regio- and Stereocontrolled Synthesis of (E)-Vinylphosphonates VIA Cross Coupling of (E)-Vinyl Iodides with Dialkyl Phosphites

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Pages 273-278 | Received 28 Jan 1999, Published online: 04 Dec 2007

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Read on this site (3)

Olga O. Kolodiazhna & Oleg I. Kolodiazhnyi. (2016) Reaction of C-silyl-P-chloro-alkylidenephosphoranes with carbonyl compounds. Phosphorus, Sulfur, and Silicon and the Related Elements 191:2, pages 322-328.
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Erzsébet Jablonkai & György Keglevich. (2014) Advances and New Variations of the Hirao Reaction. Organic Preparations and Procedures International 46:4, pages 281-316.
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Shou‐Ri Sheng, Wei Zhou, Xiao‐Ling Liu & Cai‐Sheng Song. (2004) A Convenient Selenium‐Linking Strategy for Traceless Solid‐Phase Synthesis of Diethyl 1‐Alkenephosphonates. Synthetic Communications 34:6, pages 1011-1016.
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Articles from other publishers (20)

Bianka Huszár, Renáta Szolga, Szilvia Bősze, Rita Oláhné Szabó, András Simon, Konstantin Karaghiosoff, Mátyás Czugler, László Drahos & György Keglevich. (2023) Synthesis and Anticancer Activity of Phosphinoylated and Phosphonoylated N ‐Heterocycles Obtained by the Microwave‐Assisted Palladium Acetate‐Catalyzed Hirao Reaction . Chemistry – A European Journal 29:68.
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John A. Milligan, Courtney V. Hammill, Desirae L. Crocker & Peter Wipf. 2004. Organic Reactions. Organic Reactions 457 794 .
Bianka Huszár, Petra Regina Varga, Nóra Á. Szűcs, András Simon, László Drahos & György Keglevich. (2022) Pd-Catalyzed Hirao P–C Coupling Reactions with Dihalogenobenzenes without the Usual P-Ligands under MW Conditions. Catalysts 12:10, pages 1080.
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Adam Włodarczyk. (2022) Transition metal catalyzed P–C(sp2) constructing couplings. Tetrahedron 106-107, pages 132550.
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Li Ma, Shengjie Shang, Hua Yuan, Yue Zhang, Zhigang Zeng & Yunfeng Chen. (2021) Ag(I)-catalyzed synthesis of (E)-alkenyl phosphonates by oxidative coupling of H-phosphites with β-nitroolefins. Tetrahedron Letters 87, pages 153530.
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Zhenli Xu, Zongxue Zhang, Chenxiang Meng, Xiaoya Zhang, Kai Xu, Lantao Liu, Tao Wang, Haiyun Xu & Guoliang Mao. (2021) Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E -Vinylphosphonates . Chinese Journal of Organic Chemistry 41:8, pages 3264.
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György Keglevich, Réka Henyecz & Zoltán Mucsi. (2020) Focusing on the Catalysts of the Pd- and Ni-Catalyzed Hirao Reactions. Molecules 25:17, pages 3897.
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Réka Henyecz & György Keglevich. (2019) New Developments on the Hirao Reactions, Especially from “Green” Point of View. Current Organic Synthesis 16:4, pages 523-545.
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György Keglevich, Réka Henyecz, Zoltán Mucsi & Nóra Zs. Kiss. (2017) The Palladium Acetate‐Catalyzed Microwave‐Assisted Hirao Reaction without an Added Phosphorus Ligand as a “Green” Protocol: A Quantum Chemical Study on the Mechanism. Advanced Synthesis & Catalysis 359:24, pages 4322-4331.
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Han-Sheng Lee, Shao-Hsuan Pai, Wei-Ting Liao, Xin-Jing Yang & Fu-Yu Tsai. (2017) Mono and double Mizoroki–Heck reaction of aryl halides with dialkyl vinylphosphonates using a reusable palladium catalyst under aqueous medium. RSC Advances 7:54, pages 34293-34299.
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Jin-Wei Yuan, Liang-Ru Yang, Pu Mao & Ling-Bo Qu. (2016) Silver-catalyzed synthesis of 2-arylvinylphosphonates by cross-coupling of β-nitrostyrenes with H-phosphites. RSC Advances 6:90, pages 87058-87065.
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O. I. Kolodyazhnii & A. O. Kolodyazhnaya. (2015) A new approach towards synthesis of phosphorylated alkenes. Russian Journal of General Chemistry 85:2, pages 359-365.
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Inna G. Trostyanskaya & Irina P. Beletskaya. (2014) Copper (II)-catalyzed regio- and stereoselective addition of H/P(O)R2 to alkynes. Tetrahedron 70:15, pages 2556-2562.
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Gwilherm Evano, Annie-Claude Gaumont, Carole Alayrac, Iwona E. Wrona, Joshua R. Giguere, Olivier Delacroix, Alexandre Bayle, Kévin Jouvin, Cédric Theunissen, Jérémie Gatignol & Andrew C. Silvanus. (2014) Metal-catalyzed synthesis of hetero-substituted alkenes and alkynes. Tetrahedron 70:8, pages 1529-1616.
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György Keglevich, Erzsébet Jablonkai & László B. Balázs. (2014) A “green” variation of the Hirao reaction: the P–C coupling of diethyl phosphite, alkyl phenyl- H -phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc) 2 catalyst under microwave and solvent-free conditions . RSC Adv. 4:43, pages 22808-22816.
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Sadegh Rostamnia, Abdolali Alizadeh & Long-Guan Zhu. (2008) Novel Three-Component Route to Diastereoselective Synthesis of Trisubstituted Vinylphosphonates Using Phosphites, Acetylenic Esters, and Aroyl Chlorides. Journal of Combinatorial Chemistry 11:1, pages 143-145.
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Yamina Belabassi, Saeed Alzghari & Jean-Luc Montchamp. (2008) Revisiting the Hirao cross-coupling: improved synthesis of aryl and heteroaryl phosphonates. Journal of Organometallic Chemistry 693:19, pages 3171-3178.
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Chunbo Lai, Chanjuan Xi, Weixuan Chen & Ruimao Hua. (2006) Metallo-phosphorylation of alkenes: a highly regioselective reaction of zirconocene–alkene complexes with chlorophosphate. Tetrahedron 62:26, pages 6295-6302.
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Chunyan Wang, Yuanjiang Pan & Deyu Yang. (2005) A novel stereoselective synthesis of (E)-2-arylvinylphosphonates in InCl3–NaBH4–MeCN system. Journal of Organometallic Chemistry 690:7, pages 1705-1709.
Crossref
Ping Zhong, Zhi Xing Xiong & Xian Huang. (2010) ChemInform Abstract: A Facile Regio‐ and Stereocontrolled Synthesis of (E)‐Vinylphosphonates via Cross Coupling of (E)‐Vinyl Iodides with Dialkyl Phosphites.. ChemInform 31:22.
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