Topic
Alkylation
About: Alkylation is a research topic. Over the lifetime, 29915 publications have been published within this topic receiving 464944 citations. The topic is also known as: alkylation reaction.
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TL;DR: In this article, the authors summarize some examples of novel industrial processes, based on new catalysts that are environmentally friendly, for the production of ethylbenzene and cumene, two of the most important chemicals produced by alkylation/transalkylation.
127 citations
TL;DR: Ruthenium(II) p-cymene complexes with picolyl-functionalized N-heterocyclic carbenes have been synthesized and characterized.
127 citations
TL;DR: These products are uniquely consistent with a scheme in which C8-adduct formation is preceded by an initial electrophilic substitution on the N7 atom, which is postulated to be a general reaction for activated arylamines and heterocyclic amines.
Abstract: Aromatic amines are bioactivated to electrophilic compounds that react with DNA, predominantly at the C8 position of guanine bases. This site is weakly nucleophilic and it has been proposed that the C8 adduct is the final product after initial N7-adduct formation. To consider this possibility, we reacted several C8-substituted guanine derivatives with N-acetoxy-2-aminofluorene, prepared in situ from 2-acetylsalicylic acid and N-hydroxy-2-aminofluorene. With C8,N9-dimethylguanine, an adduct was isolated in good yield that was consistent, by NMR and mass spectral characterization, with a structure involving carcinogen substitution at the N7 position of guanine and linked through the 2-aminofluorenyl nitrogen--N-(C8,N9- dimethylguanin-N7-yl)-2-aminofluorene. This adduct could be easily reduced with NaBH4, consistent with the proposed N7-adduct structure. The same reaction was also carried out with C8-methylguanosine and C8-methyldeoxyguanosine and similar adducts were isolated. In contrast, C8-bromoguanosine reacted with N-acetoxy-2-aminofluorene to yield the C8-substituted arylamine adduct N-(guanosin-C8-yl)-2-aminofluorene directly. These products are uniquely consistent with a scheme in which C8-adduct formation is preceded by an initial electrophilic substitution on the N7 atom, which is postulated to be a general reaction for activated arylamines and heterocyclic amines.
127 citations
127 citations
TL;DR: The catalytic alkylation of amide derivatives, which relies on the use of nonprecious metal catalysis, to yield ketone products is reported, underscoring the mild nature of this chemistry and its potential utility in pharmaceutical synthesis.
Abstract: We report the catalytic alkylation of amide derivatives, which relies on the use of nonprecious metal catalysis. Amide derivatives are treated with organozinc reagents, utilizing nickel catalysis, to yield ketone products. The methodology is performed at ambient temperature and is tolerant of variation in both coupling partners. A precursor to a nanomolar glucagon receptor modulator was synthesized using the methodology, underscoring the mild nature of this chemistry and its potential utility in pharmaceutical synthesis. These studies are expected to further promote the use of amides as synthetic building blocks.
127 citations