Literature DB >> 19156189

Revisiting the Hirao Cross-coupling: Improved Synthesis of Aryl and Heteroaryl Phosphonates.

Yamina Belabassi1, Saeed Alzghari, Jean-Luc Montchamp.   

Abstract

The palladium-catalyzed cross-coupling of dialkylphosphite with aromatic electrophiles (Hirao coupling) was re-investigated. Some limitations in terms of palladium loadings and substrate reactivity are alleviated with the use of Pd(OAc)(2) complexed to 1,1'-bis(diphenylphosphino)ferrocene (dppf) as a ligand. Various aryl and heteroaryl halides are employed to deliver both known and novel substituted phosphonates. The first examples of aryl chloride couplings are also reported.

Entities:  

Year:  2008        PMID： 19156189      PMCID： PMC2587344          DOI： 10.1016/j.jorganchem.2008.07.020

Source DB:  PubMed          Journal:  J Organomet Chem        ISSN： 0022-328X            Impact factor:   2.369


  19 in total

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Authors:  Adrian L Schwan
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Authors:  Christian R Samanamu; Marilyn M Olmstead; Jean-Luc Montchamp; Anne F Richards
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9.  Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides.

Authors:  Dmitri Gelman; Lei Jiang; Stephen L Buchwald
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10.  Phosphorus GABA Analogues as Potential Prodrugs.

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  7 in total

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Authors:  Timothy E Rosser; Manuela A Gross; Yi-Hsuan Lai; Erwin Reisner
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3.  Efficient synthesis of ether phosphonates using trichloroacetimidate and acetate coupling methods.

Authors:  Walid Fathalla; Ibrahim A I Ali; Pavel Pazdera
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4.  Silver(i) pyridylphosphonates - synthesis, structure, stability and light-insensitivity investigation.

Authors:  Michaela Rendošová; Róbert Gyepes; Miroslav Almáši; Ingrida Bártová; Zuzana Vargová
Journal:  RSC Adv       Date:  2019-01-11       Impact factor: 4.036

5.  The Palladium Acetate-Catalyzed Microwave-Assisted Hirao Reaction without an Added Phosphorus Ligand as a "Green" Protocol: A Quantum Chemical Study on the Mechanism.

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Journal:  Adv Synth Catal       Date:  2017-12-12       Impact factor: 5.837

Review 6.  Focusing on the Catal. of the Pd- and Ni-Catalyzed Hirao Reactions.

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7.  Palladium-Catalyzed C-P Bond-Forming Reactions of Aryl Nonaflates Accelerated by Iodide.

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  7 in total

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