Literature DB >> 28112471

[4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium-Catalyzed Process by Tuning the Cp Ligand.

Seung Youn Hong1,2, Jisu Jeong1,2, Sukbok Chang1,2.   

Abstract

A change in reaction pathway was achieved for the first time by tuning the cyclopentadienyl (Cp) ligand used for the rhodium-catalyzed cyclization of benzamides with conjugated enynones. Depending on the Cp ligand, the reaction pathway switched between [4+2] and [4+1] annulation. Electronic effects turned out to be crucial for the product distribution. The dichotomy was attributed to the alteration of the Lewis acidity of the resultant Cp-bound rhodium species.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulations; cyclopentadienyl ligands; reaction mechanisms; rhodium catalysis

Year:  2017        PMID： 28112471     DOI： 10.1002/anie.201612559

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


  9 in total

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Authors:  Chaofan Xu; Joseph P Tassone; Brandon Q Mercado; Jonathan A Ellman
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3.  Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Melissa A Ashley; Maria Romanova-Michaelides; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2018-07-23       Impact factor: 15.419

4.  Insights into the Activation Mode of α-Carbonyl Sulfoxonium Ylides in Rhodium-Catalyzed C-H Activation: A Theoretical Study.

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5.  Ru(ii)-catalyzed C6-selective C-H acylmethylation of pyridones using sulfoxonium ylides as carbene precursors.

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6.  Preparation of Cu cluster catalysts by simultaneous cooling-microwave heating: application in radical cascade annulation.

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7.  Ruthenium-catalyzed cascade C-H activation/annulation of N-alkoxybenzamides: reaction development and mechanistic insight.

Authors:  Liangliang Song; Xiaoyong Zhang; Xiao Tang; Luc Van Meervelt; Johan Van der Eycken; Jeremy N Harvey; Erik V Van der Eycken
Journal:  Chem Sci       Date:  2020-09-28       Impact factor: 9.825

8.  Rh-catalyzed aerobic oxidative cyclization of anilines, alkynes, and CO.

Authors:  Xinyao Li; Jun Pan; Hao Wu; Ning Jiao
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825

Review 9.  Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C-C Bond Forming Reactions.

Authors:  Risto Savela; Carolina Méndez-Gálvez
Journal:  Chemistry       Date:  2021-02-02       Impact factor: 5.236
  9 in total

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