41575-21-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 2898, 1994 DOI: 10.1021/jo00089a042

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 2642-63-9 3',4'-dichloroacetophenone 
• 20667-19-0 methyltriphenylphosphonium iodide 
• 124-63-0 methanesulfonyl chloride 
• 3744-74-9 2-(3,4-dichlorophenyl)propan-2-ol 
• 108-24-7 acetic anhydride 

Downstream Products

• 51-44-5 3,4-dichlorbenzoic acid 
• 875852-47-4 4-acetoxy-2-(3,4-dichloro-phenyl)-but-1-ene 
• 272775-65-2 3-(3',4'-dichlorophenyl)-3-buten-1-ol 

Relevant academic research and scientific papers

An Aliphatic Bischler-Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

The N-chloroformylimidazolidinone derivative of enantiopure l-alanine was deprotonated to form an enolate and functionalized with a series of allylic halides. Treatment of the resulting carbamoyl chlorides with potassium iodide led to cyclization of the allylic substituent onto the carbonyl group in an intramolecular aliphatic Friedel-Crafts-type acylation that corresponds to an aliphatic Bischler-Napieralski reaction. The product 3,4-dihydropyridinones were amenable to further functionalization, and finally hydrolysis, to deliver a series of enantio-enriched pipecolic acid derivatives.

Regiocontrolled synthesis of α-sulfonylmethyl o-nitrostyrenes via ZnI2-mediated sulfonylation and AgNO2/Pd(PPh3)4-promoted o-nitration

We report herein the AgNO2/Pd(PPh3)4-promoted regiocontrolled o-nitration of α-sulfonylmethylstyrenes in MeNO2 with good yields. The o-nitration process provides a series of sulfonyl o-nitrostyrenes. Substituted α-sulfonylmethylstyrenes were synthesized from ZnI2-mediated sulfonylation of substituted α-methylstyrenes and sodium sulfinates (RSO2Na) in MeCN with good to excellent yields. The structures of the key products were confirmed by X-ray crystallography. A plausible mechanism has been proposed herein.

Palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane: Synthesis of homoallylic boronic esters

A palladium-catalyzed oxidative allylation of bis[(pinacolato)boryl]methane to afford the corresponding homoallylic organoboronic esters with moderate to excellent yields is reported. This novel transformation provides an efficient strategy for the construction of homoallylic organoboronic esters in one step with a broad substrate scope. It is proposed that the palladium-catalyzed oxidative allylic C-H bond activation process may be involved in the catalytic cycle.

Iodothiocyanation/Nitration of Allenes with Potassium Thiocyanate/Silver Nitrite and Iodine

Direct strategies for the iodothiocyanation and iodonitration of allenes have been developed. In this process, potassium thiocyanate/silver nitrite and molecular iodine are used as the source of SCN, ONO2and iodine to provide the desired products in moderate to good yields with high stereoselectivity. (Figure presented.).