Literature DB >> 15174845

Efficient catalysis of Nazarov cyclization using a cationic iridium complex possessing adjacent labile coordination sites.

Mesfin Janka1, Wei He, Alison J Frontier, Richard Eisenberg.   

Abstract

The dicationic Ir(III) complex [IrMe(CO)(dppe)(DIB)](BARF)2 having adjacent labile sites has been found to be a very effective catalyst for promoting the Nazarov cyclization of aryl vinyl and divinyl ketones. Spectroscopic evidence for a substate-catalyst complex before cyclization is presented. The efficiency of the cyclization is attributed to the electrophilicity of the Ir(III) complex and substrate activation via chelation.

Entities:  

Year:  2004        PMID: 15174845     DOI: 10.1021/ja049643v

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


  9 in total

1.  Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Authors:  David Lebœuf; Jie Huang; Vincent Gandon; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-26       Impact factor: 15.336

Review 2.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

3.  A highly reactive dicationic iridium(III) catalyst for the polarized Nazarov cyclization reaction.

Authors:  Tulaza Vaidya; Abdurrahman C Atesin; Ildiko R Herrick; Alison J Frontier; Richard Eisenberg
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-26       Impact factor: 15.336

4.  Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Authors:  David Lebœuf; Vincent Gandon; Jennifer Ciesielski; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2012-04-03       Impact factor: 15.419

5.  Stereoselective Nazarov cyclizations of bridged bicyclic dienones.

Authors:  Robert D Mazzola; Timothy D White; Heidi R Vollmer-Snarr; F G West
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

6.  Understanding the fate of the oxyallyl cation following Nazarov electrocyclization: sequential Wagner-Meerwein migrations and the synthesis of spirocyclic cyclopentenones.

Authors:  Jie Huang; David Lebœuf; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2011-04-05       Impact factor: 15.419

7.  Sodium Tetrakis[(3,5-trifluoromethyl)phenyl]borate (NaBArF(24)): Safe Preparation, Standardized Purification, and Analysis of Hydration.

Authors:  Neal A Yakelis; Robert G Bergman
Journal:  Organometallics       Date:  2005-07-04       Impact factor: 3.876

8.  Benzotriazolium Salts: Emergent Readily Accessible Bench-Stable Lewis Acid Catalysts.

Authors:  Tobias Danelzik; Sumi Joseph; Christian Mück-Lichtenfeld; Constantin G Daniliuc; Olga García Mancheño
Journal:  Org Lett       Date:  2022-08-16       Impact factor: 6.072

9.  Novel d-Annulated Pentacyclic Steroids: Regioselective Synthesis and Biological Evaluation in Breast Cancer Cells.

Authors:  Svetlana K Vorontsova; Anton V Yadykov; Alexander M Scherbakov; Mikhail E Minyaev; Igor V Zavarzin; Ekaterina I Mikhaevich; Yulia A Volkova; Valerii Z Shirinian
Journal:  Molecules       Date:  2020-07-31       Impact factor: 4.411

  9 in total

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