Literature DB >> 32810335

A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C-C Coupling in Air.

Gourab Kundu1, Theresa Sperger1, Kari Rissanen2, Franziska Schoenebeck1.   

Abstract

We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2 t Bu)]2 , which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C-C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C-Br, C-OTf/OFs, and C-Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C-OTf.
© 2020 The Authors. Published by Wiley-VCH GmbH.

Entities:  

Keywords:  C−C coupling; chemoselectivity; homogeneous catalysis; olefin migration; palladium

Year:  2020        PMID： 32810335      PMCID： PMC7756449          DOI： 10.1002/anie.202009115

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


  39 in total

Review 1.  Transition metal-catalyzed enantioselective hydrogenation of enamines and imines.

Authors:  Jian-Hua Xie; Shou-Fei Zhu; Qi-Lin Zhou
Journal:  Chem Rev       Date:  2010-12-17       Impact factor: 60.622

2.  A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners.

Authors:  Benito Alcaide; Pedro Almendros; Jose M Alonso
Journal:  Chemistry       Date:  2006-03-20       Impact factor: 5.236

3.  Dinuclear palladium complexes--precursors or catalysts?

Authors:  Robert S Paton; John M Brown
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-11       Impact factor: 15.336

4.  Isomerizing olefin metathesis as a strategy to access defined distributions of unsaturated compounds from fatty acids.

Authors:  Dominik M Ohlmann; Nicole Tschauder; Jean-Pierre Stockis; Käthe Goossen; Markus Dierker; Lukas J Goossen
Journal:  J Am Chem Soc       Date:  2012-08-09       Impact factor: 15.419

5.  Use of nonfunctionalized enamides and enecarbamates in asymmetric synthesis.

Authors:  Kovuru Gopalaiah; Henri B Kagan
Journal:  Chem Rev       Date:  2011-05-13       Impact factor: 60.622

6.  In situ generated bulky palladium hydride complexes as catalysts for the efficient isomerization of olefins. Selective transformation of terminal alkenes to 2-alkenes.

Authors:  Delphine Gauthier; Anders T Lindhardt; Esben P K Olsen; Jacob Overgaard; Troels Skrydstrup
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

7.  Recent advances of dinuclear nickel- and palladium-complexes in homogeneous catalysis.

Authors:  Wentao Xu; Muzi Li; Liancheng Qiao; Jin Xie
Journal:  Chem Commun (Camb)       Date:  2020-07-02       Impact factor: 6.222

Review 8.  Regioselective (site-selective) functionalization of unsaturated halogenated nitrogen, oxygen and sulfur heterocycles by Pd-catalysed cross-couplings and direct arylation processes.

Authors:  Ian J S Fairlamb
Journal:  Chem Soc Rev       Date:  2007-04-27       Impact factor: 54.564

9.  Diastereoselective palladium-catalyzed alpha-arylation of 4-substituted cyclohexyl esters.

Authors:  Eric A Bercot; Seb Caille; Tracy M Bostick; Krishnakumar Ranganathan; Randy Jensen; Margaret M Faul
Journal:  Org Lett       Date:  2008-10-28       Impact factor: 6.005

10.  Arylation of Axially Chiral Phosphorothioate Salts by Dinuclear PdI Catalysis.

Authors:  Xiang-Yu Chen; Maoping Pu; Hong-Gang Cheng; Theresa Sperger; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-09       Impact factor: 15.336
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  5 in total

1.  Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group.

Authors:  Tatjana Kreisel; Marvin Mendel; Adele E Queen; Kristina Deckers; Daniel Hupperich; Julian Riegger; Christoph Fricke; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-21       Impact factor: 16.823

2.  Air-Stable PdI Dimer Enabled Remote Functionalization: Access to Fluorinated 1,1-Diaryl Alkanes with Unprecedented Speed.

Authors:  Gourab Kundu; Filip Opincal; Theresa Sperger; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-23       Impact factor: 16.823

3.  Stereoselective tandem iridium-catalyzed alkene isomerization-cope rearrangement of ω-diene epoxides: efficient access to acyclic 1,6-dicarbonyl compounds.

Authors:  Rahul Suresh; Itai Massad; Ilan Marek
Journal:  Chem Sci       Date:  2021-06-09       Impact factor: 9.825

4.  A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C-C Coupling in Air.

Authors:  Gourab Kundu; Theresa Sperger; Kari Rissanen; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-28       Impact factor: 15.336

5.  Rapid and column-free syntheses of acyl fluorides and peptides using ex situ generated thionyl fluoride.

Authors:  Cayo Lee; Brodie J Thomson; Glenn M Sammis
Journal:  Chem Sci       Date:  2021-11-29       Impact factor: 9.825
  5 in total

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