39809-93-3

Upstream product

• 994-30-9 triethylsilyl chloride 
• 80-15-9 Cumene hydroperoxide 
• 617-86-7 triethylsilane 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 88070-48-8 N-methylbenzamide 
• 80-15-9 Cumene hydroperoxide 

Relevant academic research and scientific papers

Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons

We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel

Alkylsilyl Peroxides as Alkylating Agents in the Copper-Catalyzed Selective Mono-N-Alkylation of Primary Amides and Arylamines

The copper-catalyzed selective mono-N-alkylation of primary amides or arylamines using alkylsilyl peroxides as alkylating agents is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the alkylsilyl peroxides, as well as to the primary amides and arylamines. Mechanistic studies suggest that the present reaction should proceed through a free-radical process that includes alkyl radicals generated from the alkylsilyl peroxides.

Application of Isayama–Mukaiyama cobalt catalyzed hydroperoxysilylation for the preparation of ritonavir hydroperoxide

We report the preparation of thiazol-5-ylmethyl ((2S,3S,5S)-5-((S)-2-(3-((2-(2-hydroperoxypropan-2-yl)thiazol-4-yl)methyl)-3-methylureido)-3-methylbutanamido)-3-hydroxy-1,6-diphenylhexan-2-yl)carbamate, a hydroperoxide impurity of ritonavir also known as

Co-catalyzed autoxidation of alkene in the presence of silane. The effect of the structure of silanes on the efficiency of the reaction and on the product distribution

A systematic investigation of the structural effect of silanes on the Co-catalyzed reductive oxygenation of alkene in the presence of silane (Mukaiyama-Isayama reaction) showed that the efficiency of the reaction decreases with the increase of the steric bulk of the silanes. A similar trend was observed for the metal-exchange reaction between Co(III)-alkylperoxo complex and silane, too. The peroxidation of (S)-limonene, followed by deprotection of the derived silyl peroxides, provides a mixture of the corresponding monocyclic hydroperoxide 24 and the bicyclic one 25, the ratio being a marked function of the steric bulk of silanes.

Synthesis of cyclic peroxides by chemo- and regioselective peroxidation of dienes with Co(II)/O2/Et3SiH

(Chemical Equation Presented). In the competitive peroxidation of mixtures of two alkenes with Co(II)/O2/Et3SiH, it was found that the relative reactivities of the alkene substrates are influenced by three major factors:. (1) relative stability of the intermediate carbon-centered radical formed by the reaction of the alkene with HCo(III) complex, (2) steric effects around the C=C double bond, and (3) electronic factors associated with the C=C double bond. Consistent with results from simple alkenes, the chemo-and regioselective peroxidation of dienes was also realized. Depending on the diene structure, the product included not only the expected acyclic unsaturated triethylsilyl peroxides but also 1,2-dioxolane and 1,2-dioxane derivatives via intramolecular cyclization of the unsaturated peroxy radical intermediates.

Co(thd)2: A superior catalyst for aerobic epoxidation and hydroperoxysilylation of unactivated alkenes: Application to the synthesis of spiro-1,2,4-trioxanes

Bis(2,2,6,6-tetramethyl-3,5-heptanedionato)cobalt(II) (Co(thd) 2), a β-diketonate prepared in a simple one-step procedure, is an excellent catalyst for aerobic epoxidation and Mukaiyama-Isayama hydroperoxysilylation of unactivated alkenes. For hydroperoxysilylation, Co(thd)2 is superior to Co(acac)2 and can catalyse oxidation of cyclic alkenes in excellent yield. Chiral β-diketonate or keto iminato catalysts failed to catalyse this reaction in an enantioselective manner and a free radical mechanism consistent with this observation is proposed. Hydroperoxysilylation of cyclohex-1-enylmethanol by Co(thd) 2 followed by addition of a ketone/TsOH provides a simple one-pot procedure for the synthesis of spiro-1,2,4-trioxane antimalarials.

Co(III)-alkyl complex- and Co(III)-alkylperoxo complex-catalyzed triethylsilylperoxidation of alkenes with molecular oxygen and triethylsilane

ROOCo(III) + Et3SiH → ROOSiEt3 + [HCo(III)] cat. ROOCo(III) or cat. RCo(III) R'CH=CH2 → R'CH(OOSiEt3)CH3 Et3SiH, O2 Both a Co(III)-alkyl complex and a Co(III)-alkylperoxo complex were found to catalyze triethylsilylperoxidation of alkenes with O2 and Et3SiH. On this basis, together with the nonstereoselectivity in the Co(II)-catalyzed peroxidation of 3-phenylindene and the formation of the corresponding 1,2-dioxolane from 2-phenyl-1-vinylcyclopropane (a radical clock), we propose a reasonable mechanism for the Co(II)-catalyzed novel autoxidation of alkenes with Et3SiH discovered by Isayama and Mukaiyama.

Novel Method for the Preparation of Triethylsilyl Peroxides from Olefins by the Reaction with Molecular Oxygen and Triethylsilane Catalyzed by Bis(1,3-diketonato)cobalt(II)

In the presence of a catalytic amount of bis(1,3-diketonato)cobalt(II), various olefins react with molecular oxygen and triethylsilane at room temperature to give the corresponding triethylsilyl peroxides in high yields under neutral conditions.The reaction provides a new method for the preparation of various peroxides directly from olefins.