Literature DB >> 26449465

Complete Switch of Selectivity in the C-H Alkenylation and Hydroarylation Catalyzed by Iridium: The Role of Directing Groups.

Jiyu Kim1,2, Sung-Woo Park1,2, Mu-Hyun Baik1,2, Sukbok Chang1,2.   

Abstract

A complete switch in the Cp*Ir(III)-catalyzed paths between C-H olefination and hydroarylation was found to be crucially dependent on the type of directing groups. This dichotomy in product distribution was correlated to the efficiency in attaining syn-coplanarity of olefin-inserted 7-membered iridacycles. Theoretical studies support our hypothesis that the degree of flexibility of this key intermediate modulates the β-H elimination, which ultimately affords the observed chemoselectivity.

Entities:  

Year:  2015        PMID: 26449465     DOI: 10.1021/jacs.5b09824

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


  8 in total

1.  A directing group switch in copper-catalyzed electrophilic C-H amination/migratory annulation cascade: divergent access to benzimidazolone/benzimidazole.

Authors:  Hasina Mamataj Begam; Shantanu Nandi; Ranjan Jana
Journal:  Chem Sci       Date:  2022-04-14       Impact factor: 9.969

2.  The C-H activated controlled mono- and di-olefination of arenes in ionic liquids at room temperature.

Authors:  Kaifeng Du; Tian Yao
Journal:  RSC Adv       Date:  2020-01-20       Impact factor: 4.036

3.  Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.

Authors:  Adam B Weinstein; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-06-23       Impact factor: 6.005

Review 4.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

5.  Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling.

Authors:  Qian Wu; Ying Chen; Dingyuan Yan; Muyue Zhang; Yi Lu; Wei-Yin Sun; Jing Zhao
Journal:  Chem Sci       Date:  2016-08-03       Impact factor: 9.825

6.  Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome.

Authors:  Noelia Casanova; Karina P Del Rio; Rebeca García-Fandiño; José L Mascareñas; Moisés Gulías
Journal:  ACS Catal       Date:  2016-04-14       Impact factor: 13.084

7.  Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides.

Authors:  Wu Yang; Yingzi Li; Jiefeng Zhu; Wentan Liu; Jie Ke; Chuan He
Journal:  Chem Sci       Date:  2020-09-03       Impact factor: 9.825

8.  Carboxylate-directed C-H allylation with allyl alcohols or ethers.

Authors:  Xiao-Qiang Hu; Zhiyong Hu; A Stefania Trita; Guodong Zhang; Lukas J Gooßen
Journal:  Chem Sci       Date:  2018-05-21       Impact factor: 9.825

  8 in total

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