72596-31-7

Upstream product

• 769-92-6 4-tert-Butylaniline 
• 61765-93-3 p-tert-butylphenylhydrazine 
• 122-52-1 triethyl phosphite 
• 84563-54-2 bis(4-tert-butylphenyl)iodonium trifluoromethanesulfonate 
• 1262384-87-1 (4-(tert-butyl)phenyl)triethoxysilane 
• 762-04-9 phosphonic acid diethyl ester 
• 59970-38-6 4-tert-butylphenyl mesylate 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 154318-75-9 4-tert-butylphenyl triflate 

Downstream Products

• 128333-50-6 (4-tert-Butyl-phenyl)-phosphonic acid monohexyl ester 
• 100134-03-0 4-tert-butylphenyl phosphonic acid 

Relevant academic research and scientific papers

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

Microwave assisted P–C coupling reactions without directly added P-ligands

Our group introduced a green protocol for the Pd(OAc)2- or NiCl2-catalyzed P–C coupling reaction of aryl halides and various > P(O)H-compounds under MW conditions without directly added P-ligands. The reactivity of a few aryl derivatives in the Pd(OAc)2-catalyzed Hirao reaction was also studied. An induction period was observed in the reaction of bromobenzene and diphenylphosphine oxide. Finally, the less known copper(I)-promoted P–C coupling reactions were investigated experimentally. The mechanism was explored by quantum chemical calculations.

Photoinduced transition-metal and external photosensitizer free cross-coupling of aryl triflates with trialkyl phosphites

Photoinduced phosphonation of aryl triflates with trialkyl phosphites via a tandem single-electron-transfer, C-O bond cleavage and Arbuzov rearrangement process in the absence of transition-metal and external photosensitizer is reported herein. The protoc

Visible-Light-Mediated Metal-Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations

This work describes a straightforward access to a large variety of aryl phosphonates by the simple combination of diaryliodonium salts with phosphites in the presence of a base and under visible-light illumination. The reaction proceeds smoothly, tolerates various functionalities, and was applied for the synthesis of pharmaceutically relevant compounds. Mechanistic investigations, including EPR, NMR, and DFT calculations, support the postulated reaction mechanism.

Avisible-light-promoted metal-free strategy towards arylphosphonates: Organic-dye-catalyzed phosphorylation of arylhydrazines with trialkylphosphites

A visible-light-induced metal-free catalytic system was developed for the synthesis of arylphosphonates starting from arylhydrazines and trialkylphosphites. By using the inexpensive eosin B as catalyst, sub-stoichiometric amounts of DABCO, and ambient air as oxidant, diverse arylphosphonates were obtained under visible-light irradiation. Notably, this catalytic system is suitable for gram-scale reaction by utilizing sunlight as an illumination source.

Ar-P bond construction by the Pd-catalyzed oxidative cross-coupling of arylsilanes with H-phosphonates via C-Si bond cleavage

A novel and efficient methodology that allows for the construction of Ar-P bonds via the Pd-catalyzed oxidative cross-coupling reaction of various arylsilanes with H-phosphonates leading to valuable arylphosphonates has been developed.

Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates

The first general palladium catalyst for the phosphorylation of aryl mesylates and tosylates is reported. The newly developed system exhibits excellent functional group compatibility. For instance, free amino, keto, ester, and amido groups, as well as het

MW-Assisted P-C Coupling Reaction Using P-Ligand-Free Pd(OAc) 2 Catalyst

P-C coupling reactions of a variety of >P(O)H species with aryl bromides were found to take place under P-ligand-free microwave conditions.

Palladium-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with H-phosphonate diesters

A novel and convenient palladium-catalyzed cross-coupling reaction of H-phosphonate diesters with sodium arylsulfinates was developed via desulfitation in the presence of silver carbonate and tetra-butylammonium chloride. This method is highly efficient and provides a rapid access to a broad spectrum of arylphosphonate diesters in good to excellent yields.

Palladium-catalyzed desulfitative C-P coupling of arylsulfinate metal salts and H-phosphonates

Catalyzed by palladium(ii) chloride, a diverse range of arylsulfinate sodium, potassium, lithium, silver, zinc, and copper salts undergo desulfination/C-P coupling with H-phosphonates, in the presence of silver(i) carbonate as oxidant, to produce useful arylphosphonates under microwave irradiation. the Partner Organisations 2014.