65853-51-2

Upstream product

• 696-62-8 para-iodoanisole 
• 351531-29-8 O-potassio-3,3-dimethyl-2-butanone 
• 79958-53-5 (E)-1-(3,3-dimethylbut-1-en-1-yl)-4-methoxybenzene 
• 17510-46-2 3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene 
• 104-94-9 4-methoxy-aniline 
• 2393-23-9 4-methoxy-benzylamine 
• 66582-09-0 1-(3,3-dimethylbut-1-yn-1-yl)-4-methoxybenzene 
• 64723-95-1 pinacolone enolate anion 
• 29800-93-9 diethyl phosphite 
• 1512864-18-4 2,2'-(2,2-dimethylpropane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 153822-76-5 1-(4-hydroxyphenyl)-3,3-dimethylbutan-2-one 
• 53365-39-2 1-(4-methoxyphenyl)-3,3-dimethylbutan-2-amine 
• 153822-84-5 1-(3,5-dibromo-4-hydroxyphenyl)-3,3-dimethylbutan-2-one oxime 
• 153822-77-6 1-(3,5-dibromo-4-hydroxyphenyl)-3,3-dimethylbutan-2-one 
• 153822-83-4 1-(4-hydroxyphenyl)-3,3-dimethylbutan-2-one oxime 

Relevant academic research and scientific papers

Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(i) complexes

We have investigated the role of ring sizes and substituents in NHC ligands in some (NHC)Au(i) complexes in the hydration of internal alkynes. Despite the fact that using (NHC)Au(i) complexes in the hydration of diarylacetylenes leads to Markovnikov-type products, the precise tuning of ligands allows changing the regioselectivity in arylalkylacetylene hydration to the anti-Markovnikov-type.

Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage

The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.

Salicylic Acid-Catalyzed Arylation of Enol Acetates with Anilines

α-Aryl ketones are both structure moieties commonly found in bioactive compounds and versatile synthetic intermediates for the preparation of drug-like molecules. An operationally simple and scalable protocol has been developed to prepare α-aryl ketones from readily available aromatic amines and enol acetates (or silyl enol ethers). This metal-free methodology features the use of salicylic acid as a convenient catalyst to promote the formation of aryl radicals from in-situ generated aryl diazonium salts, without demanding thermal or photochemical activation. The mild reaction conditions used are compatible with anilines substituted with diverse functionalities. Structural elaboration of some prepared α-aryl ketones was accomplished to illustrate their usefulness as building blocks. (Figure presented.).

Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds

We report a transition-metal-free coupling of aldehydes and ketones with geminal bis(boron) building blocks which provides the coupled, homologated carbonyl compound upon oxidation. This reaction not only extends an alkyl chain containing a carbonyl group, it also simultaneously introduces a new carbonyl substituent. We demonstrate that enantiopure aldehydes with an enolizable stereogenic center undergo this reaction with complete retention of stereochemistry.

Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation

The allylic hydrogen is found to have a dramatic effect on the regioselectivity of the Wacker oxidation, leading to the postulation that an agostic hydrogen or enyl (σ + π) complex helps to stabilise the key intermediate.

THE EFFECT OF ORTHO SUBSTITUENTS IN SRN1 REACTIONS. SOME SYNTHETIC APPLICATIONS.

Several ortho-substituted iodobenzenes were allowed to react, via the SRNl mechanism, with mixtures of diethyl phosphite ion and pinacolone enolate ion.From product composition data, the relative reactivities of the two nucleophiles were reckoned.They represent relative reactivities in attachment to aryl radical intermediates.Most of the ortho effects are slight, but there is evidence that large ortho substituents hinder attachment of the phosphite more than the enolate nucleophile.The methoxy and diethoxyphosphoryl substituents, when para to the site of substitution, respectively favour and disfavour the phosphite with respect to the enolate ion.SRNl reactions of ortho-substituted halobenzenes are, for some substituents, followed by other reactions which afford products of synthetic interest.