ArticleCurrent organic synthesis2019
New Developments on the Hirao Reactions, Especially from "Green" Point of View.
Article in Current organic synthesis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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9 citing papers in PubMed.
- Article
- Microwave-Assisted Palladium Acetate-Catalyzed C-P Cross-Coupling of Arylboronic Acids and >P(O)H Reagents in the Absence of the Usual Mono- and Bidentate P-Ligands: Mechanistic Insights.The Journal of organic chemistry · 2023Article
- C-P bond formation of cyclophanyl-, and aryl halidesRSC advances · 2022Article
- Enantioseparation ofThe Journal of organic chemistry · 2021Article
- Microwaves as "Co-Catalysts" or as Substitute for Catalysts in Organophosphorus Chemistry.Molecules (Basel, Switzerland) · 2021Review
- Experimental and Theoretical Study on the "2,2'-Bipiridyl-Ni-Catalyzed" Hirao Reaction of >P(O)H Reagents and Halobenzenes: A Ni(0) → Ni(II) or a Ni(II) → Ni(IV) Mechanism?The Journal of organic chemistry · 2020Article
- Focusing on the Catal. of the Pd- and Ni-Catalyzed Hirao Reactions.Molecules (Basel, Switzerland) · 2020Review
- Denitrative Cross-Couplings of Nitrostyrenes.Molecules (Basel, Switzerland) · 2020Review
- Continuous Flow Esterification of aMolecules (Basel, Switzerland) · 2020Article
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Authors and funding
2 authors.
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Abstract
backgroundThe Hirao reaction discovered ca. 35 years ago is an important P-C coupling protocol between dialkyl phosphites and aryl halides in the presence of Pd(PPh3)4 as the catalyst and a base to provide aryl phosphonates. Then, the reaction was extended to other Preagents, such as secondary phosphine oxides and H-phosphinates and to other aryl and hetaryl derivatives to afford also phosphinic esters and tertiary phosphine oxides. Instead of the Pd(PPh3)4 catalyst, Pd(OAc)2 and Ni-salts were also applied as catalyst precursors together with a number of mono- and bidentate P-ligands.
objectiveIn our review, we undertook to summarize the target reaction with a special stress on the developments attained in the last 6 years, hence this paper is an update of our earlier reviews in a similar topic.
conclusions"Greener" syntheses aimed at utilizing phase transfer catalytic and microwave-assisted approaches, even under "P-ligand-free. or even solvent-free conditions are the up-to date versions of the classical Hirao reaction. The mechanism of the reaction is also in the focus these days.
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