109202-53-1

Upstream product

• 53215-95-5 N-(trimethylsilylmethyl)benzylamine 
• 100-39-0 benzyl bromide 
• 2344-80-1 Chloromethyltrimethylsilane 
• 103-49-1 dibenzylamine 
• 100-46-9 benzylamine 
• 4206-67-1 iodo(trimethylsilyl)methane 

Downstream Products

• 1619229-76-3 C₇₅H₁₇N 

Relevant academic research and scientific papers

SET-promoted photoaddition reactions of N-α-trimethylsilylmethyl-N,N-dibenzylamines with fullerene C60. Electronic factors that govern photoaddition efficiencies

Single electron transfer (SET) promoted photoaddition reactions of N-α-trimethylsilylmethyl-N,N-dibenzylamines to fullerene C60 were investigated as part of an effort aimed at developing a general method to prepare various aryl ring containing aminomethylfullerenes and exploring factors that govern photoaddition efficiencies. The results show that the photoaddition reactions take place highly efficiently to form 1,2-adducts. The mechanism for this process involves generation of aminium radicals and C60 anion radical intermediates by a pathway initiated by excited state SET. SET is followed by desilylation of the aminium radicals to produce α-amino radicals that couple with either C60 or its radical anion to form precursors of the 1,2-adducts. The electronic nature of para-substituents on the aryl ring of N-α-trimethylsilylmethyl-N,N-dibenzylamines has a pronounced effect on the efficiency of the photoaddition reaction, with electron donating groups causing a greater than 2-fold enhancement compared to that brought about by electron withdrawing groups.

Selective 1,2-Aryl-Aminoalkylation of Alkenes Enabled by Metallaphotoredox Catalysis

A highly chemo- and regioselective intermolecular 1,2-aryl-aminoalkylation of alkenes by photoredox/nickel dual catalysis is described here. This three-component conjunctive cross-coupling is highlighted by its first application of primary alkyl radicals, which were not compatible in previous reports. The readily prepared α-silyl amines could be transferred to α-amino radicals by photo-induced single electron transfer step. The radical addition/cross-coupling cascade reaction proceeds under mild, base-free and redox-neutral conditions with good functional group tolerance, and importantly, provides an efficient and concise method for the synthesis of structurally valuable α-aryl substituted γ-amino acid derivatives motifs.

Method for the synthesis of amine-functionalized fullerenes involving set-promoted photoaddition reactions of -silylamines

A novel method for the preparation of structurally diverse fullerene derivatives, which relies on the use of single electron transfer (SET)-promoted photochemical reactions between fullerene C60 and α-trimethylsilylamines, has been developed. Photoirradiation of 10% EtOH-toluene solutions containing C60 and α-silylamines leads to high-yielding, regioselective formation of 1,2-adducts that arise through a pathway in which sequential SET-desilylation occurs to generate α-amino and C60 anion radical pair intermediates, which undergo C-C bond formation. Protonation of generated α-aminofullerene anions gives rise to formation of monoaddition products that possess functionalized α-aminomethyl-substituted 1,2-dihydrofullerene structures. Observations made in this effort show that the use of EtOH in the solvent mixture is critical for efficient photoproduct formation. In contrast to typical thermal and photochemical strategies devised previously for the preparation of fullerene derivatives, the new photochemical approach takes place under mild conditions and does not require the use of excess amounts of substrates. Thus, the method developed in this study could broaden the scope of fullerene chemistry by providing a simple photochemical strategy for large-scale preparation of highly substituted fullerene derivatives. Finally, the α-aminomethyl-substituted 1,2-dihydrofullerene photoadducts are observed to undergo photoinduced fragmentation reactions to produce C60 and the corresponding N-methylamines.

Substituent effects on the benzyl groups in Sommelet-Hauser rearrangement

The effects of substituents (MeO, Me, H, Br, CN, NO2) of the benzyl groups in the Sommelet-Hauser rearrangement of N,N-bis(substituted benzyl)-N-methyl(trimethylsilyl)methylammonium halides with cesium fluoride in N,N-dimethylformamide were exa