Literature DB >> 25113317

Versatile Cu(I)/Pd(0) dual catalysis for the synthesis of quaternary α-allylated carbonyl compounds: development, mechanistic investigations and scope.

Fady Nahra1, Yohan Macé, Arnaud Boreux, Francois Billard, Olivier Riant.   

Abstract

We report herein a versatile cooperative dual catalysis reaction based on a Cu(I)/Pd(0) system. Mechanistic investigation shows that every component plays a crucial role in determining the reaction outcome. The reaction is successfully extended to various substrates; such as α,β-unsaturated ketones, malonates and coumarins. The strategy tolerates different substitution patterns and affords good yields for each family of substrates.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylation; asymmetric; copper; dual catalysis; palladium

Year:  2014        PMID: 25113317     DOI: 10.1002/chem.201404015

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  7 in total

1.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

2.  Enantioselective Preparation of Arenes with β-Stereogenic Centers: Confronting the 1,1-Disubstituted Olefin Problem Using CuH/Pd Cooperative Catalysis.

Authors:  Zhaohong Lu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-30       Impact factor: 15.336

3.  A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors:  Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

4.  Enantioselective Hydrocarbamoylation of Alkenes.

Authors:  Sheng Feng; Yuyang Dong; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823

5.  Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones.

Authors:  Robert A Craig; Steven A Loskot; Justin T Mohr; Douglas C Behenna; Andrew M Harned; Brian M Stoltz
Journal:  Org Lett       Date:  2015-10-26       Impact factor: 6.005

6.  Asymmetric Hydroarylation of Vinylarenes Using a Synergistic Combination of CuH and Pd Catalysis.

Authors:  Stig D Friis; Michael T Pirnot; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

Review 7.  The Allylic Alkylation of Ketone Enolates.

Authors:  Lukas Junk; Uli Kazmaier
Journal:  ChemistryOpen       Date:  2020-09-10       Impact factor: 2.630

  7 in total

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