83188-09-4

Upstream product

• 31366-05-9 (±)2-methyl-1-phenylpentan-1-one 
• 141-97-9 ethyl acetoacetate 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 14583-98-3 1-tributylstannanyl-propan-2-one 
• 28483-60-5 Acetonyltributylstananne 
• 65700-06-3 percarbonate de O,O-tert-butyle et O-isopropyle 
• 93-55-0 1-phenyl-propan-1-one 
• 94287-27-1 tert-butyldimethyl((1-phenylprop-1-en-1-yl)oxy)silane 
• 76886-61-8 4-methyl-5-phenylhex-5-en-2-one 
• 3102-33-8 trans-3-penten-2-one 
• 611-73-4 Benzoylformic acid 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 625-33-2 3-penten-2-one 
• 98-88-4 benzoyl chloride 

Downstream Products

• 90904-38-4 3,5-dimethyl-2-phenylfuran 

Relevant academic research and scientific papers

Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C?H Bond Activation

Photoredox-catalyzed isomerization of γ-carbonyl-substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C?H bond activation. This catalytic redox-neutral process resulted in the synthesis of 1,4-dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density functional theory calculations show that the carbonyl group at the γ-position of allylic alcohols are beneficial to the formation of their corresponding allylic alcohol radicals with high vertical electron affinity, which contributes to the completion of the photoredox catalytic cycle.

Photoredox-Catalyzed Generation of Acetonyl Radical in Flow: Theoretical Investigation and Synthetic Applications

A hydrogen atom transfer (HAT) step from acetone allowed the smooth generation of acetonyl radical that was then exploited as synthon in the mild formation of C-C bonds under flow conditions. The process was promoted by aryl radicals photocatalytically generated via single-electron transfer (SET) reduction of arenediazonium salts. The mechanism has been investigated by a combined experimental and computational approach and further supported by deuterium labeling experiments.

Visible-Light-Promoted Synthesis of 1,4-Dicarbonyl Compounds via Conjugate Addition of Aroyl Chlorides

A facile visible-light photocatalytic conjugate addition to prepare 1,4-dicarbonyl compounds has been developed by employing readily available aroyl chlorides as aryl radical sources. This operationally simple method shows a broad scope with regard to both aroyl chlorides and Michael acceptors. As a result, a variety of 1,4-diketones were efficiently synthesized in moderate to good yields.

An iron-catalyzed hydroalkylation reaction of α,β-unsaturated ketones with ethers

A general strategy for the hydroalkylation of vinyl ketones using ethers catalyzed by an iron catalyst is described. This catalytic method permits direct transformation of easily accessible and abundant precursors into highly substituted, structurally diverse and functionally concentrated products.

Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group

We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the α-halocarbonyls, which are usually generated in the presence of fluoride anions or Lewis acids. A variety of silyl enol ethers, α-bromoketones, α-bromoesters, and α-bromoamides were applied to this system to produce the coupling compounds.

Decarboxylative 1,4-Addition of α-Oxocarboxylic Acids with Michael Acceptors Enabled by Photoredox Catalysis

Enabled by iridium photoredox catalysis, 2-oxo-2-(hetero)arylacetic acids were decarboxylatively added to various Michael acceptors including α,β-unsaturated ester, ketone, amide, aldehyde, nitrile, and sulfone at room temperature. The reaction presents a new type of acyl Michael addition using stable and easily accessible carboxylic acid to formally generate acyl anion through photoredox-catalyzed radical decarboxylation.

Oxidative Generation of α-Radicals of Carbonyl Compounds from the α-Stannyl Derivatives and Their Reactions with Electron-Rich Olefins

The oxidation of α-tributylstannyl alkanoates with tetrabutylammonium hexanitratocerate(IV) generates α-radicals of the alkanoates by eliminating the stannylium ion.The thus-formed radicals react with various electron-rich olefinic compounds, such as silyl enol ethers, giving addition products in good yield.This method formally achieves selective cross coupling between alkanoates and ketones.

Isomerization of 4-aryl-4-methylhex-5-en-2-ones to 5-aryl-4-methylhex-5-en-2-ones by an intramolecular ene-retro ene reaction sequence

Acid-catalyzed thermal rearrangement of 4-aryl-4-methylhex-5-en-2-ones (products of the Claisen rearrangement of β-methylcinnamyl alcohols and 2-methoxypropene) to isomeric 5-aryl-4-methylhex-5-en-2-ones via an intramolecular ene reaction of the enol taut

Catalytic Effect of Five-Coordinate Organotin Bromide or Tetraphenylstibonium Bromide on the Chemo- and Stereoselective Addition of Tin Enolate to α-Halo Ketone

Two types of catalysts, five-coordinate organotin bromides and tetraphenylstibonium bromide, similarly promoted the selective addition of tin enolates to the carbonyl moiety in α-halo ketones.The reaction with 2-chlorocyclohexanones and the enolates gave

Facile Control of Regioselectivity in the Reaction of Tin Enolates with α-Halogeno Carbonyls by Additives

Tin enolates 1 reacted with α-halogeno ketones 2 and esters 10 to give a variety of 1,4-diketones 3 and γ-keto esters 11, respectively, in the presence of appropriate additives such as hexamethylphosphoric triamide (HMPT), tributylphosphine oxide and tetrabutylammonium bromide, while complexation of these additives with tributyltin bromide allowed catalytic production of β-keto oxiranes 4 instead of 3.The reaction mechanism for the preparation of 1,4-diketone 3 is discussed.