7616-91-3

Upstream product

• 3282-32-4 2-diazo-acetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 146514-98-9 tert-butyl hypofluorite 
• 4747-13-1 α-methoxystyrene 
• 75-65-0 tert-butyl alcohol 
• 507-19-7 t-butyl bromide 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 98-88-4 benzoyl chloride 
• 6343-27-7 1-benzoylpyrrolidine-2,5-dione 
• 1634-04-4 tert-butyl methyl ether 
• 100-42-5 styrene 
• 75-91-2 tert.-butylhydroperoxide 
• 75-05-8 acetonitrile 
• 507-40-4 tert-butylhypochlorite 

Downstream Products

• 79598-02-0 2-(tert-Butoxy)-1,3-diphenyl-propan-1,3-dion 
• 79597-92-5 2-(tert-Butoxy)-1-hydroxy-1,3-diphenyl-1-propen-2-on 
• 33193-70-3 2-Hydroxy-2-methoxy-1,3-diphenylpropan-1,3-dion 
• 643-75-4 1,3-diphenyl-propane-1,2,3-trione 

Relevant academic research and scientific papers

Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.

Highly Selective Synthesis of 2- tert-Butoxy-1-Arylethanones via Copper(I)-Catalyzed Oxidation/ tert-Butoxylation of Aryl Olefins with TBHP

A practical and environmentally friendly protocol for the selective oxidation of aryl olefins to arylethanone derivatives by using a Cu(I) catalyst and tert-butyl hydroperoxide (TBHP) has been developed. A series of 2-tert-butoxy-1-arylethanones were obtained in moderate to good yields under mild conditions with high selectivity. In this method, TBHP acts not only as an oxidant but also as the tert-butoxy and carbonyl oxygen sources. This enables one-step oxidation/tert-butoxylation. Various allyl peroxides were also synthesized from allyl substrates.

Synthesis of alkynyl ethers and low-temperature sigmatropic rearrangement of allyl and benzyl alkynyl ethers

(Chemical Equation Presented) α-Alkoxy ketones 3 can be transformed into 1-alkynyl ethers 5 by a two-step procedure involving formation of the enol triflate or phosphate and base-induced elimination. Performing the same reaction sequence with allylic alcohols (R2OH, R2 = allyl) furnishes instead γ,δ-unsaturated carboxylic acid derivatives 6, derived from [3,3]-sigmatropic rearrangement of the intermediate allyl alkynyl ethers at -78 °C and trapping of the subsequently formed ketene with nucleophiles (Nu-H). Benzyl alkynyl ether 5 (R2 = benzyl) rearranges to indanone 7 upon heating to 60 °C.

A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from α-oxy-substituted derivatives through no

The photooxidation of 2′-deoxyguanosine (dG) and its derivative 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG) by a series of acetophenones (AP-X) and benzophenone (BP) has been studied. The favorable absorption characteristics of the benzoyl chromophore e

Indium triflate: A mild and efficient Lewis acid catalyst for O-H insertion reactions of α-diazo ketones

Facile O-H insertion reactions of α-diazo ketones with aliphatic/aromatic alcohols or benzenethiol have been developed in the presence of indium triflate as a catalyst. These reactions provided good yields of α-alkoxy ketones. A comparative study with other Lewis acids establishes the reactivity of indium triflate in O-H insertion reactions of α-diazo ketones.

Tert-Butyl Hypofluorite - An Electrophilic tert-Butoxylation Agent

tert-Butyl hypofluorite, t-BuOF, easily synthesized from Z-BuOH and F2, is a unique source of the novel electrophilic tert-butoxylium moiety t-BuO+. It was added to several benzylic double bonds to form vicinal fluoro-tert-butoxide derivatives. Not surprisingly, this bulky reagent is quite sensitive to steric hindrance. The process is electrophilic in nature, but since the reaction is relatively slow (20-60 min) formation of various radical species can take place, forming eventually several distinct byproducts. t-BuOF was also reacted with a number of enols, producing the corresponding α-tert-butoxy ketone derivatives in moderate to good yields. The best results were obtained with benzylic enol derivatives.

A NEW METHOD FOR THE DIRECT INTRODUCTION OF ALKOXYL GROUP TO SILYL ENOL ETHER WITH ALKYL HIPOCHLORITE CATALYZED BY PALLADIUM(0)

α-Alkoxyketones and α-ketoacetals are prepared in good yields from silyl enol ethers and alkyl hypochlorites catalyzed by tetrakis(triphenylphosphine)palladium(0).