Literature DB >> 29750383

Nickel-Catalyzed Coupling of Arylzinc Halides with Thioesters.

Paul H Gehrtz1, Prasad Kathe1, Ivana Fleischer1.   

Abstract

The Pd-catalyzed Fukuyama reaction of thioesters with organozinc reagents is a mild, functional-group-tolerant method for acylation chemistry. Its Ni-catalyzed variant might be a sustainable alternative to expensive catalytic Pd sources. We investigated the reaction of S-ethyl thioesters with aryl zinc halides with hetero- and homotopic Ni precatalysts and several ligands. The results show that both homo- and heterotopic species may contribute to catalysis. The substrate scope using an operationally homogeneous defined Ni complex was established. Acyl radicals are postulated as short-lived intermediates.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Fukuyama coupling; acyl radicals; ketones; nickel catalysis; thioester

Year:  2018        PMID: 29750383     DOI: 10.1002/chem.201801887

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


  3 in total

1.  Decarbonylative Sulfide Synthesis from Carboxylic Acids and Thioesters via Cross-Over C-S Activation and Acyl Capture.

Authors:  Chengwei Liu; Michal Szostak
Journal:  Org Chem Front       Date:  2021-06-22       Impact factor: 5.456

2.  Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates.

Authors:  Philippe Klein; Vivien Denise Lechner; Tanja Schimmel; Lukas Hintermann
Journal:  Chemistry       Date:  2019-11-26       Impact factor: 5.236

3.  Cobalt-catalyzed acylation-reactions of (hetero)arylzinc pivalates with thiopyridyl ester derivatives.

Authors:  Ferdinand H Lutter; Lucie Grokenberger; Maximilian S Hofmayer; Paul Knochel
Journal:  Chem Sci       Date:  2019-07-11       Impact factor: 9.825

  3 in total

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