92368-72-4

Upstream product

• 3761-92-0 n-hexylmagnesium bromide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 4282-40-0 1-Iodoheptane 
• 76376-91-5 n-heptyl phenyl selenide 
• 100-66-3 methoxybenzene 
• 13125-66-1 n-heptylmagnesium bromide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 254454-47-2 4-methoxyphenylzinc iodide 

Downstream Products

• 857230-10-5 4-(5-heptyl-2-methoxy-phenyl)-4-oxo-butyric acid 
• 860745-23-9 acetic acid-(5-heptyl-2-hydroxy-anilide) 
• 81259-72-5 2-nitro-4-heptylphenol 
• 669092-10-8 2-Amino-4-heptyl-phenol 
• 1987-50-4 p-heptylphenol 

Relevant academic research and scientific papers

Reevaluation of the Palladium/Carbon-Catalyzed Decarbonylation of Aliphatic Aldehydes

An improved method for the decarbonylation of aliphatic aldehydes by using a commercially available Pd/C catalyst is described. The reaction conditions are suitable for linear, cyclic, or sterically demanding substrates, as they afford the corresponding alkanes in yields of up to 99%. In addition, this Pd/C-catalyzed method exhibits good functional-group tolerance. A comparison of previously reported methods with the present one showed that the reaction conditions play a crucial role in the outcome of the reaction. The method can also be applied in a two-step reaction sequence for the synthesis of industrially important compounds.

P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis

p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.

Nitrous oxide-dependent iron-catalyzed coupling reactions of grignard reagents

The formation of carbon-carbon bonds is one of the fundamental transformations in chemistry. In this regard the application of palladium-based catalysts has been extensively investigated during recent years, but nowadays research focuses on iron catalysis, due to sustainability, costs and toxicity issues; hence numerous examples for iron-catalyzed cross-coupling reactions have been established, based on the coupling of electrophiles (R1-X, X = halide) with nucleophiles (R2-MgX). Only a small number of protocols deals with the iron-catalyzed oxidative coupling of nucleophiles (R1-MgX + R2-MgX) with the aid of oxidants (1,2-dihaloethanes). However, some issues arise with these oxidants; hence more recently the potential of the industrial waste product nitrous oxide (N2O) was investigated, because the unproblematic side product N2 is formed. Based on that, we demonstrate the catalytic potential of easily accessible iron complexes in the oxidative coupling of Grignard reagents. Importantly, nitrous oxide was essential to obtain yields up to 99% at mild conditions (e.g. 1 atm, ambient temperature) and low catalyst loadings (0.1 mol%) Excellent catalyst performance is realized with turnover numbers of up to 1000 and turnover frequencies of up to 12000 h-1. Moreover, a good functional group tolerance is observed (e.g. amide, ester, nitrile, alkene, alkyne). Afterwards the reaction of different Grignard reagents revealed interesting results with respect to the selectivity of cross-coupling product formation.

Negishi alkyl-aryl cross-coupling catalyzed by Rh: Efficiency of novel tripodal 3-diphenylphosphino-2-(diphenylphosphino)methyl-2-methylpropyl acetate ligand

3-Diphenylphosphino-2-(diphenylphoshino)methyl-2-methylpropyl acetate acted as an efficient ligand for a Rh catalyst, achieving cross-coupling between arylzinc compounds bearing electron-withdrawing groups and alkyl electrophiles. The beneficial effect of the tripodal ligand and such aryl nucleophiles was discussed with regard to the specificity of the Rh catalysis.

New One-pot Cross-coupling Reaction between Grignard Reagents and Alkoxymethyldiphenylphosphonium Iodides in situ-Formed from Alcohols, Chlorodiphenylphosphine and Iodomethane

A new one-pot cross-coupling reaction between Grignard reagents and alkoxymethyldiphenylphosphonium iodides, which were in situ-formed from nBuLi-treated alcohols, chlorodiphenylphosphine and iodomethane, proceeded smoothly to afford the corresponding coupling products in good to high yields.