3245-93-0

Upstream product

• 112497-43-5 N-allyl-N-methyl-4-toluene sulphonamide 
• 178905-39-0 3-[1,1-bis(methylethyl)-2-methyl-1-silapropoxy]propane-1-ol 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 47528-43-8 N-<2-(2-Methoxy-phenoxy)-aethyl>-3--propylamin 
• 3245-96-3 N-Methyl-N-<3-brom-propyl>-p-toluolsulfonsaeure-amid 

Relevant academic research and scientific papers

Catalytic Hydroalkylation of Allenes

We have developed a catalytic method for the hydroalkylation of allenes using alkyl triflates as electrophiles and silane as a hydride source. The reaction has an excellent substrate scope and is compatible with a wide range of functional groups, including esters, aryl halides, aryl boronic esters, sulfonamides, alkyl tosylates, and alkyl bromides. We found evidence for a reaction mechanism that involves unusual dinuclear copper ally complexes as catalytic intermediates. The unusual structure of these complexes provides a rationale for their unexpected reactivity.

Free-radical hydroxylation reactions of alkylboronates

The radical hydroxylation of B-alkylcatecholboranes, easily prepared by hydroboration of olefins, has been investigated. When molecular oxygen was used as oxidizing agent, the corresponding alcohols were obtained directly without alkaline treatment. The presence of Lewis base additives such as Et3N or DABCO has a benefic effect on the selectivity and yield. Alternatively, 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) reacts cleanly with B-alkylcatecholboranes to afford alkyl radicals that can be trapped by a second equivalent of TEMPO to give alkoxyamines. Reduction of the alkoxyamines with zinc in acetic acid affords the desired alcohols. The whole procedure is particularly mild and does not require any basic condition. The two approaches presented in this paper are valuable and represent mild alternatives to the classical alkaline oxidation of organoboranes to alcohols.

Hydroxylation of olefins using molecular oxygen via alkylboronic esters

Alkylboronic esters derived from olefins undergo a hydroxylation in the presence of triethylamine and molecular oxygen. Alcohols were obtained in good to excellent yields without alkaline treatment of the boronate ester intermediates. Radical-clock experiments allowed the comparison between radical and polar reaction paths.