Literature DB >> 21417401

Palladium-catalyzed mono-α-arylation of acetone with aryl halides and tosylates.

Kevin D Hesp1, Rylan J Lundgren, Mark Stradiotto.   

Abstract

We report the first example of selective Pd-catalyzed mono-α-arylation of acetone employing aryl chlorides, bromides, iodides, and tosylates. The use of appropriately designed P,N-ligands proved to be the key to controlling the reactivity and selectivity. The reaction affords good yields with substrates containing a range of functional groups at modest Pd loadings using Cs(2)CO(3) as the base and employing acetone as both a reagent and the solvent.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID: 21417401     DOI: 10.1021/ja200009c

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


  6 in total

1.  Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C-Cl site.

Authors:  Zicong Chen; Changxue Gu; On Ying Yuen; Chau Ming So
Journal:  Chem Sci       Date:  2022-03-16       Impact factor: 9.969

2.  Intramolecular transannulation of alkynyl triazoles via alkyne-carbene metathesis step: access to fused pyrroles.

Authors:  Yi Shi; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005

3.  Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols.

Authors:  Guangfan Zheng; Yan Li; Jingjie Han; Tao Xiong; Qian Zhang
Journal:  Nat Commun       Date:  2015-04-22       Impact factor: 14.919

4.  Catalytic α-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.

Authors:  Enrico Marelli; Martin Corpet; Yury Minenkov; Rifahath M Neyyappadath; Alessandro Bismuto; Giulia Buccolini; Massimiliano Curcio; Luigi Cavallo; Steven P Nolan
Journal:  ACS Catal       Date:  2016-03-30       Impact factor: 13.084

5.  Iminophosphanes: Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles.

Authors:  Mark K Rong; Koen van Duin; Tom van Dijk; Jeroen J M de Pater; Berth-Jan Deelman; Martin Nieger; A W Ehlers; J Chris Slootweg; Koop Lammertsma
Journal:  Organometallics       Date:  2017-02-16       Impact factor: 3.876

6.  Vinyl Cation Stabilization by Silicon Enables a Formal Metal-Free α-Arylation of Alkyl Ketones.

Authors:  Amandine Pons; Jean Michalland; Wojciech Zawodny; Yong Chen; Veronica Tona; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-22       Impact factor: 15.336

  6 in total

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