Literature DB >> 26882088

Catalytic Selenium-Promoted Intermolecular Friedel-Crafts Alkylation with Simple Alkenes.

E Tang1, Yinjiao Zhao1, Wen Li1, Weilin Wang1, Meng Zhang1, Xin Dai1.   

Abstract

A method for conducting selenium-promoted intermolecular Friedel-Crafts (F-C) alkylation reactions has been developed with simple alkenes using trimethylsilyl trifluoromethanesulfonate as a catalyst and N-phenylselenophthalimide as an efficient selenium source. Electron-rich arenes smoothly underwent F-C alkylation with a variety of alkenes to afford alkylated products in good yield and with high regioselectivity and diastereoselectivity. The regioselectivity and stereoselectivity of arenes and alkenes as well as a preliminary mechanism of the F-C alkylation reaction are discussed.

Entities:  

Year:  2016        PMID: 26882088     DOI: 10.1021/acs.orglett.5b03579

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Rhodium-catalyzed cascade reactions of triazoles with organoselenium compounds - a combined experimental and mechanistic study.

Authors:  Fang Li; Chao Pei; Rene M Koenigs
Journal:  Chem Sci       Date:  2021-03-24       Impact factor: 9.825

2.  Fe(OTf)3-catalysed Friedel-Crafts reaction of benzenoid arenes with α,β-unsaturated carbonyl compounds: easy access to 1,1-diarylalkanes.

Authors:  Aditya Bhattacharya; Pushpendra Mani Shukla; Biswajit Maji
Journal:  R Soc Open Sci       Date:  2017-10-25       Impact factor: 2.963

3.  Efficient Protocol for Synthesis of β-Hydroxy(alkoxy)selenides via Electrochemical Iodide-Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides.

Authors:  Jinyang Chen; Lan Mei; Haiying Wang; Li Hu; Xiaorui Sun; Jianwei Shi; Qiang Li
Journal:  ChemistryOpen       Date:  2019-09-10       Impact factor: 2.911

  3 in total

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