70728-98-2

Upstream product

• 330980-08-0 ((CH₃C₆H₄)3PC₆H₃(C₄H₉)CH₃PdI)2 
• 13716-12-6 tri-tert-butyl phosphine 
• 98-51-1 4-tert-butyltoluene 
• 85336-17-0 5-tert-butyl-2-methylaniline 

Downstream Products

• 98910-94-2 5-t-Butyl-2-methylbenzenephosphonic acid monoethyl ester 
• 98910-95-3 2-(Bromomethyl)-5-t-butylbenzenephosphonic acid monoethyl ester 
• 144381-50-0 sodium monoethyl 5-tert-butyl-1-(oxymethyl-15-crown-5)methylbenzenephosphonate 
• 330980-08-0 [Pd(P(o-tolyl)3)(2-Me-5-t-Bu-C6H3)(μ-I)]2 
• 98910-93-1 diethyl 5-tert-butyl-2-methylbenzenephosphonate 

Relevant academic research and scientific papers

Cyclic Hypervalent Iodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed Ring Expansion

Azides are building blocks of increasing importance in synthetic chemistry, chemical biology, and materials science. Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. Herein, we report a safety study of ABX, which shows its hazardous nature. We introduce two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile, and use them in established photoredox- and metal-mediated azidations, and in a new ring-expansion of silylated cyclobutanols to give azidated cyclopentanones.

Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones

A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.

A metal-free direct C (sp3)-H cyanation reaction with cyanobenziodoxolones

A metal-free protocol of direct C(sp3)-H cyanation with cyanobenziodoxolones functioning as both cyanating reagents and oxidants was developed. Unactivated substrates, such as alkanes, ethers and tertiary amines, were thereby transformed to the corresponding nitriles in moderate to high yields. Mechanistic studies indicated that the cyanation proceeded with two potential pathways, which is highly dependent on the substrates: (1) a free radical case for alkanes and ethers and (2) an oxidative case for tertiary amines.

Rapid aerobic iodination of arenes mediated by hypervalent iodine in fluorinated solvents

Arenes are rapidly converted to the corresponding iodides by aerobic oxidative iodination at room temperature by treatment with iodine and catalytic quantities of nitrous acid in a fluorinated solvent. Dichloroiodic acid is proposed as the actual iodination reagent.

Iodine(I) reagents in hydrochloric acid-catalyzed oxidative iodination of aromatic compounds by hydrogen peroxide and iodine

Hydrochloric acid activates the oxidative iodination of aromatic compounds with the iodine- hydrogen peroxide system through the formation of an iodine(I) compound as the iodinating reagent. Activation with hydrochloric acid is more powerful than that with sulfuric acid. The formation of dichloroiodic(I) acid (HICl2) with various forms of hydrogen peroxide was followed using UV spectroscopy. The HICl2 was used as the iodinating reagent. In the preparative oxidative iodinaton of various aromatic compounds, hydrochloric acid was used in a catalytic amount and the iodine(I) reagent was formed in situ with 0.5 equiv. hydrogen peroxide and 0.5 equiv. molecular iodine. Two types of reactivity were observed in oxidative iodination with iodine(I) species catalyzed by hydrochloric acid: in the iodination of anisole 1a better yields of iodination were observed with a smaller amount of hydrochloric acid, while on the contrary 4-tert-butyltoluene 1b gave better yields of iodination upon increasing the amount of hydrochloric acid. Reactivity was further manipulated by the choice of the solvent (MeCN, trifluoroethanol, hexafluoro-2-propanol). Copyright

Aerobic oxidative iodination of organic molecules activated by sodium nitrite

Aerobic oxidative iodination activated by sodium nitrite occurs effectively and selectively with 100% iodine atom economy with air as the oxidant. Silica-supported sulfuric acid was used for the activation of the catalyst and iodination. Thus, I2/NaNO2/air/silica-supported H2SO4 in acetonitrile iodinated aromatics, ketones and aldehydes effectively at ambient temperature.

Progressive direct iodination of sterically hindered alkyl substituted benzenes

Benzene derivatives bearing at least one bulky alkyl group (i-Pr or t-Bu) were selectively and effectively iodinated using elemental iodine activated, by 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor, F-TED

Synthesis of Lipophilic Crown Ethers with Pendant Phosphonic Acid or Phosphonic Acid Monoethyl Ester Groups

Synthetic routes to fifteen lipophilic crown ether phosphonic acid monoethyl esters and nine lipophilic crown ether phosphonic acids are described.For both classes of crown ethers which have pendant, proton-ionizable groups, the crown ether ring sizes are

Side Arm Participation in Crown Phosphonate Monoethyl Ester-Alkali Metal Cation Complexes

Paticipation of an anionic side group in complexation of a polyether-bound alkali metal cation in solution is demonstrated by (1)H n.m.r. spectroscopy.