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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.


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Journal ArticleDOI
Hai-Lei Cui1, Xin Feng1, Jing Peng1, Jie Lei1, Kun Jiang1, Ying-Chun Chen1 
TL;DR: The research group has reported that modified cinchona alkaloids are outstanding catalysts for the asymmetric allylic alkylation of a,a-dicyanoolefins with MBH carbonates and the deprotonation of the acidic NH group of the MBH base.
Abstract: The indole framework represents a key structural motif in a large number of biologically active natural products and pharmaceutical compounds. Consequently, modifications on the indole structure, including the development of enantioselective variants, have triggered increasing interests. Because of the inherent nucleophilic characteristics of indole compounds, their reactions preferentially take place at the C3-position of the ring system. As a result, the majority of enantioselective reactions of indoles focus on the C3-selective addition of electron-rich indoles to electrophilic imines, epoxides, carbonyl compounds, a,b-unsaturated carbonyl compounds, and nitroalkenes etc., thus leading to the formation of diversely structured enantioenriched C3-functionalized indole derivatives. Recently, the enantioselective synthesis of C2-substituted indoles has also been realized through the asymmetric alkylation of 4,7-dihydroindoles and subsequent oxidation. In sharp contrast to the progress in enantioselective alkylation at the C3or C2-positions, the asymmetric Nalkylation of indoles has been underdeveloped: probably because of the privileged C3-chemoselectivity of indole compounds. The limited examples include the palladiumcatalyzed N-allylic alkylation of 3-substituted indoles developed by Trost et al. and the enantioselective intramolecular aza-Michael addition of tethered indole-2-carboxylates under chiral phase-transfer catalysis developed by Bandini et al. Indeed, N-alkylated indoles have been applied as useful intermediates for the synthesis of polyheterocycles and occur widely among natural products and biologically active pharmaceuticals (Scheme 1). For example, mitomycin C exhibits potent antitumour activity and is used clinically in the treatment of certain cancers. Yuremamine, which was recently isolated from the stem bark of Mimosa hostilis, shows hallucinogenic and psychoactive effects. Pyrrolo[3,2,1-ij]quinoline derivatives are active antihistamines and inhibitors of leukotriene, and they offer the possibility of a novel multimediator approach to the treatment of allergic diseases. Therefore, it would be extremely desirable to develop effective protocols to access optically pure N-alkylated indoles. Recently, the allylic alkylation of Morita-Baylis–Hillman (MBH) adducts catalyzed by a metal-free organic Lewis base has emerged as an attractive strategy to prepare multifunctional compounds. Our research group has also reported that modified cinchona alkaloids are outstanding catalysts for the asymmetric allylic alkylation of a,a-dicyanoolefins with MBH carbonates. We anticipated that, as outlined in Scheme 2, the deprotonation of the acidic NH group of the

209 citations

Journal ArticleDOI
TL;DR: The present emerging area deals with the recent advances in the use of pi-activated alcohols in the catalytic and stereoselective construction of benzylic stereocenters.
Abstract: The direct functionalization of aromatic compounds, via Friedel–Crafts alkylation reactions with alcohols, is one of the cornerstones in organic chemistry. The present emerging area deals with the recent advances in the use of π-activated alcohols in the catalytic and stereoselective construction of benzylic stereocenters.

208 citations

Journal ArticleDOI
TL;DR: The carbenium ion mechanism in the formation of various aliphatic (C1,C6) and aromatic (C6,C10) hydrocarbons was studied in this article.

208 citations

Journal ArticleDOI
TL;DR: In this article, the HBEA-supported Pd catalyst optimally balances the competing rates of metal catalyzed hydrogenation as well as of solid acid-catalyzed dehydration and carbon-carbon coupling to combine hydrodeoxygenation and dimerization of phenol derivatives to C-12-C-18 bicycloalkanes.

208 citations

Journal ArticleDOI
TL;DR: A general and benign iron-catalyzed α-alkylation reaction of ketones with primary alcohols has been developed and using 2-aminobenzyl alcohol as alkylation reagent allows for the "green" synthesis of quinoline derivatives.
Abstract: A general and benign iron-catalyzed α-alkylation reaction of ketones with primary alcohols has been developed. The key to success of the reaction is the use of a Knolker-type complex as catalyst (2 mol %) in the presence of Cs2 CO3 as base (10 mol %) under hydrogen-borrowing conditions. Using 2-aminobenzyl alcohol as alkylation reagent allows for the "green" synthesis of quinoline derivatives.

208 citations


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