Literature DB >> 24905079

Cu-catalyzed cascades to carbocycles: union of diaryliodonium salts with alkenes or alkynes exploiting remote carbocations.

Fengzhi Zhang1, Shoubhik Das, Andrew J Walkinshaw, Alicia Casitas, Michael Taylor, Marcos G Suero, Matthew J Gaunt.   

Abstract

Copper-catalyzed cascade reactions between alkenes or alkynes and diaryliodonium salts form carbocyclic products in a single step. Arylation of the unsaturated functional group is proposed to form a carbocation intermediate that facilitates hydride shift pathways to translocate the positive charge to a remote position and enables ring formation via a Friedel-Crafts-type reaction.

Entities:  

Year:  2014        PMID： 24905079     DOI： 10.1021/ja504361y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  5 in total

1.  Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations.

Authors:  Qilei Zhu; Emily C Gentry; Robert R Knowles
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-12       Impact factor: 15.336

2.  Electrochemical Fluorination of Vinyl Boronates through Donor-Stabilized Vinyl Carbocation Intermediates.

Authors:  Benjamin Wigman; Woojin Lee; Wenjing Wei; Kendall N Houk; Hosea M Nelson
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-03       Impact factor: 15.336

3.  Enantioselective and Regiodivergent Copper-Catalyzed Electrophilic Arylation of Allylic Amides with Diaryliodonium Salts.

Authors:  Elise Cahard; Henry P J Male; Matthieu Tissot; Matthew J Gaunt
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419

4.  DFT calculations on the mechanism of copper-catalysed tandem arylation-cyclisation reactions of alkynes and diaryliodonium salts.

Authors:  Tamás Károly Stenczel; Ádám Sinai; Zoltán Novák; András Stirling
Journal:  Beilstein J Org Chem       Date:  2018-07-12       Impact factor: 2.883

5.  Palladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: a stoichiometric heavy metal-free and user-friendly approach.

Authors:  Zhongxing Huang; Quynh P Sam; Guangbin Dong
Journal:  Chem Sci       Date:  2015-06-17       Impact factor: 9.825
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.