Literature DB >> 26276904

Single-Flask Multicomponent Palladium-Catalyzed α,γ-Coupling of Ketone Enolates: Facile Preparation of Complex Carbon Scaffolds.

Michael Grigalunas1, Per-Ola Norrby1,2, Olaf Wiest1,3, Paul Helquist4.   

Abstract

A three-component palladium-catalyzed reaction sequence has been developed in which γ-substituted α,β-unsaturated products are obtained in a single flask by an α-alkenylation with either a subsequent γ-alkenylation or γ-arylation of a ketone enolate. Coupling of a variety of electronically and structurally different components was achieved in the presence of a Pd/Q-Phos catalyst (2 mol %), usually at 22 °C with yields of up to 85 %. Most importantly, access to these products is obtained in one simple operation in place of employing multiple reactions.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cross-coupling; ketones; multicomponent reactions; palladium; synthetic methods

Year:  2015        PMID: 26276904     DOI: 10.1002/anie.201505895

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


  3 in total

1.  Palladium-Catalyzed Selective α-Alkenylation of Pyridylmethyl Ethers with Vinyl Bromides.

Authors:  Xiaodong Yang; Byeong-Seon Kim; Minyan Li; Patrick J Walsh
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

2.  A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Authors:  Stephen D Holmbo; Nicole A Godfrey; Joshua J Hirner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2016-09-16       Impact factor: 15.419

3.  Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Authors:  Chuan Liu; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-15       Impact factor: 15.336

  3 in total

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