Literature DB >> 27739637

Trapping σ-Alkyl-Palladium(II) Intermediates with Arynes Encompassing Intramolecular C-H Activation: Spirobiaryls through Pd-Catalyzed Cascade Reactions.

Marta Pérez-Gómez1, José-Antonio García-López2.   

Abstract

A palladium-catalyzed cascade reaction based on the trapping of transient alkyl-PdII intermediates with arynes encompassing a C-H activation step has been developed. This synthetic pathway gives rise to hetero-spirocyclic scaffolds containing a biaryl motif, and opens up new synthetic strategies in the design of cascade reactions since it gathers several aspects of Pd chemistry, i.e., intra- and intermolecular carbopalladation of unsaturated species, C-H activation and C-C coupling processes.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; aryne; carbopalladation; cascade reactions; spirocycles

Year:  2016        PMID: 27739637     DOI: 10.1002/anie.201607976

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


  4 in total

1.  Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements.

Authors:  Christine A Dimirjian; Marta Castiñeira Reis; Edward I Balmond; Nolan C Turman; Elys P Rodriguez; Michael J Di Maso; James C Fettinger; Dean J Tantillo; Jared T Shaw
Journal:  Org Lett       Date:  2019-09-05       Impact factor: 6.005

2.  Regioselective synthesis of spirocyclic pyrrolines via a palladium-catalyzed Narasaka-Heck/C-H activation/[4 + 2] annulation cascade reaction.

Authors:  Wan-Xu Wei; Xiangtao Kong; Rui-Qiang Jiao; Xue-Song Li; Cui-Tian Wang; Yuke Li; Yong-Min Liang
Journal:  Chem Sci       Date:  2022-05-06       Impact factor: 9.969

3.  Exploring the mechanism of the Pd-catalyzed spirocyclization reaction: a combined DFT and experimental study.

Authors:  Ivan Franzoni; Hyung Yoon; José-Antonio García-López; Amalia Isabel Poblador-Bahamonde; Mark Lautens
Journal:  Chem Sci       Date:  2017-12-08       Impact factor: 9.825

4.  Synthesis of Spiroindenyl-2-Oxindoles through Palladium-Catalyzed Spirocyclization of 2-Bromoarylamides and Vinyl Bromides.

Authors:  Shuai Yang; Yanghui Zhang
Journal:  Molecules       Date:  2021-12-10       Impact factor: 4.411

  4 in total

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