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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.


Papers
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Journal ArticleDOI
TL;DR: The catalytic performance of zeolite β in the liquid-phase alkylation of benzene is compared with that of other solid catalysts as discussed by the authors, and a hypothesis to explain this behavior is given.

292 citations

Journal ArticleDOI
TL;DR: The reaction is catalyzed by Cu(OAc)2 and a Ag2CO3 cocatalyst, and shows high generality and functional-group tolerance, as well as providing a straightforward means for the preparation of ortho-aminobenzoic acid derivatives.
Abstract: New methods for direct arylation, alkylation, and oxygenation of sp2 carbon-hydrogen bonds in directing-group containing benzenes have resulted in efficient synthetic routes to functionalized arenes.[1] In contrast, direct amination reactions that do not proceed via nitrenoid intermediates[2] are relatively rare. In most cases, palladium catalysis is used for aminations.[3a-p] Furthermore, majority of publications describe intramolecular C-N bond formation.[3a-i] Typically, protected amines or hydroxylamine derivatives are used to install nitrogen moiety. Simple amine coupling partners are employed only rarely. Several deprotonative, copper-catalyzed thiazole and oxazole aminations have been reported.[4b,c,e] Yu has reported a method for palladium-catalyzed benzamide amination by employing a removable auxiliary.[3k] We disclose here a method for an auxiliary-assisted amination of non-acidic benzamide β-C–H bonds and benzylamine derivative γ-C–H bonds that is catalyzed by copper(II) acetate.

291 citations

Book ChapterDOI
TL;DR: This chapter deals with the formation and metabolism of alkylated purines in nucleic acids and briefly discusses other alkylation reactions leading to the alkylphosphate triester production andAlkylated pyrimidines.
Abstract: Publisher Summary Alkylation of nucleic acids occurs both physiologically within living cells and after the administration of compounds that are either themselves direct chemical alkylating agents or are converted into alkylating agents by metabolic activation. Some of these compounds are highly potent carcinogens. Carcinogenicity of these agents is due to the alkylation of certain cellular components because no other degradation product nor is the compound itself oncogenic. This chapter deals with the formation and metabolism of alkylated purines in nucleic acids. It briefly discusses other alkylation reactions leading to the alkylphosphate triester production and alkylated pyrimidines. It also presents evidences favoring particular critical targets for the action of alkylating carcinogens. The attack on nucleic acids by carcinogenic alkylating agents is not entirely random and generally leads to the formation of alkylated nucleosides at many different sites distributed throughout the cellular nucleic acids. Carcinogenesis is not necessarily mediated through mutagenesis in somatic cells. However, it is observed that carcinogenic action could be mediated through a distinct action of the electrophilic reactant.

290 citations

Journal ArticleDOI
TL;DR: A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles was developed based on a norbornene-mediated regioselective cascade C-H activation, and two structurally different Aspidosperma alkaloids were synthesized in concise routes.
Abstract: A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles was developed based on a norbornene-mediated regioselective cascade C–H activation. The detailed reaction mechanism was investigated by NMR spectroscopic analyses, characterization of the key intermediate, deuterium labeling experiments, and kinetic studies. The results indicate that a catalytic cycle operates, in which an N-norbornene type palladacycle is formed as the key intermediate. Oxidative addition of alkyl bromide to the Pd(II) center in this intermediate is the rate-determining step of the reaction. The synthetic utility of this indole 2-alkylation method was demonstrated by its application in natural product total synthesis. A new and general strategy to synthesize Aspidosperma alkaloids was established employing the indole 2-alkylation reaction as the key step, and two structurally different Aspidosperma alkaloids, aspidospermidine and goniomitine, were synthesized in concise routes.

289 citations

Journal ArticleDOI
TL;DR: A norbornene-mediated palladium-catalyzed tandem alkylation/C-H functionalization sequence is described, in which an alkyl-aryl bond and a heteroaryl- Daryl bond are formed in one pot.
Abstract: A norbornene-mediated palladium-catalyzed tandem alkylation/C−H functionalization sequence is described, in which an alkyl−aryl bond and a heteroaryl−aryl bond are formed in one pot. A variety of highly substituted six- and seven-membered ring annulated indoles were synthesized in good yields from bromoalkyl indoles and aryl iodides.

289 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023652
20221,161
2021561
2020516
2019630
2018631