Literature DB >> 28466531

Nickel-Catalyzed α-Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols.

Yann Bernhard1, Brodie Thomson1, Vincent Ferey2, Mathieu Sauthier1.   

Abstract

An additive-free nickel-catalyzed α-allylation of aldehydes with allyl alcohol is reported. The reaction is promoted by 1 mol % of in situ formed nickel complex in methanol, and water is the sole by-product of the reaction. The experimental conditions allow the conversion of various α-branched aldehydes and α,β-unsaturated aldehydes as nucleophiles. The same catalyst and reaction conditions enabled a tandem aldol condensation of aldehyde/α-allylation reaction.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aldehydes; allylations; allylic alcohols; homogeneous catalysis; nickel

Year:  2017        PMID： 28466531     DOI： 10.1002/anie.201703486

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  5 in total

1.  Identifying the Imperative Role of Metal-Olefin Interactions in Catalytic C-O Reductive Elimination from Nickel(II).

Authors:  Trevor D Lohrey; Alexander Q Cusumano; William A Goddard; Brian M Stoltz
Journal:  ACS Catal       Date:  2021-08-02       Impact factor: 13.700

Review 2.  Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts.

Authors:  Lars Süsse; Brian M Stoltz
Journal:  Chem Rev       Date:  2021-02-11       Impact factor: 60.622

3.  Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols.

Authors:  Aurapat Ngamnithiporn; Carina I Jette; Shoshana Bachman; Scott C Virgil; Brian M Stoltz
Journal:  Chem Sci       Date:  2018-01-24       Impact factor: 9.825

4.  Case Study of N-i Pr versus N-Mes Substituted NHC Ligands in Nickel Chemistry: The Coordination and Cyclotrimerization of Alkynes at [Ni(NHC)2 ].

Authors:  Lukas Tendera; Moritz Helm; Mirjam J Krahfuss; Maximilian W Kuntze-Fechner; Udo Radius
Journal:  Chemistry       Date:  2021-11-16       Impact factor: 5.020

5.  Deconjugative α-Alkylation of Cyclohexenecarboxaldehydes: An Access to Diverse Terpenoids.

Authors:  Rachid Chahboun; José Manuel Botubol-Ares; María Jesús Durán-Peña; Fermín Jiménez; Ramón Alvarez-Manzaneda; Enrique Alvarez-Manzaneda
Journal:  J Org Chem       Date:  2021-06-15       Impact factor: 4.354
  5 in total

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