Literature DB >> 19590747

Ruthenium Vinyl Carbene Intermediates in Enyne Metathesis.

Steven T Diver1.   

Abstract

This review provides an overview of ruthenium vinyl carbene reactivity as it relates to enyne metathesis. Methods for the synthesis of metathesis-active and metathesis-inactive complexes are also summarized. Some of the early hypotheses about vinyl carbene intermediates in enyne metatheses were tested in the arena of synthetic chemistry and subsequently led to mechanistic studies. In these two areas, studies from the author's labs are described. There are still many unresolved questions in enyne metathesis that trace back to vinyl carbene reactivity. Hopefully this review will stimulate further investigation into vinyl carbene reactivity which should further refine our understanding of catalytic enyne metathesis.

Entities:  

Year:  2007        PMID: 19590747      PMCID: PMC2707033          DOI: 10.1016/j.ccr.2006.09.008

Source DB:  PubMed          Journal:  Coord Chem Rev        ISSN: 0010-8545            Impact factor:   22.315


  34 in total

1.  The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

Authors:  T M Trnka; R H Grubbs
Journal:  Acc Chem Res       Date:  2001-01       Impact factor: 22.384

2.  Synthesis of trisubstituted alkenes via olefin cross-metathesis.

Authors:  A K Chatterjee; R H Grubbs
Journal:  Org Lett       Date:  1999-12-02       Impact factor: 6.005

3.  Rate enhancement by ethylene in the Ru-catalyzed ring-closing metathesis of enynes: evidence for an "ene-then-yne" pathway that diverts through a second catalytic cycle.

Authors:  Guy C Lloyd-Jones; Robert G Margue; Johannes G de Vries
Journal:  Angew Chem Int Ed Engl       Date:  2005-12-01       Impact factor: 15.336

4.  Carbon monoxide-promoted carbene insertion into the aryl substituent of an N-heterocyclic carbene ligand: Buchner reaction in a ruthenium carbene complex.

Authors:  Brandon R Galan; Milan Gembicky; Paulina M Dominiak; Jerome B Keister; Steven T Diver
Journal:  J Am Chem Soc       Date:  2005-11-16       Impact factor: 15.419

5.  Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors:  B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

6.  Alkenylcarbene ruthenium arene complexes as initiators of alkene metathesis: an enyne creates a catalyst that promotes its selective transformation.

Authors:  Ricardo Castarlenas; Matthieu Eckert; Pierre H Dixneuf
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-22       Impact factor: 15.336

7.  A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis.

Authors:  Varinder K Aggarwal; Christopher J Astle; Mark Rogers-Evans
Journal:  Org Lett       Date:  2004-04-29       Impact factor: 6.005

8.  Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions.

Authors:  Soon Hyeok Hong; Michael W Day; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2004-06-23       Impact factor: 15.419

9.  Cycloheptadiene ring synthesis by tandem intermolecular enyne metathesis.

Authors:  Amol A Kulkarni; Steven T Diver
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

10.  Ring closing enyne metathesis: control over mode selectivity and stereoselectivity.

Authors:  Eric C Hansen; Daesung Lee
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

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  6 in total

1.  Equilibrium between a cyclotrisilene and an isolable base adduct of a disilenyl silylene.

Authors:  Michael J Cowley; Volker Huch; Henry S Rzepa; David Scheschkewitz
Journal:  Nat Chem       Date:  2013-09-15       Impact factor: 24.427

Review 2.  Stable cyclic carbenes and related species beyond diaminocarbenes.

Authors:  Mohand Melaimi; Michèle Soleilhavoup; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

3.  Cyclic alkyl amino carbene (CAAC) ruthenium complexes as remarkably active catalysts for ethenolysis.

Authors:  Vanessa M Marx; Alexandra H Sullivan; Mohand Melaimi; Scott C Virgil; Benjamin K Keitz; David S Weinberger; Guy Bertrand; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-17       Impact factor: 15.336

4.  Divergent, C-C Bond Forming Macrocyclizations Using Modular Sulfonylhydrazone and Derived Substrates.

Authors:  Wenqing Xu; Lauren E Brown; John A Porco
Journal:  J Org Chem       Date:  2021-11-03       Impact factor: 4.354

5.  Organic-inorganic hybrid silica material derived from a monosilylated Grubbs-Hoveyda ruthenium carbene as a recyclable metathesis catalyst.

Authors:  Guadalupe Borja; Roser Pleixats; Ramón Alibés; Xavier Cattoën; Michel Wong Chi Man
Journal:  Molecules       Date:  2010-08-23       Impact factor: 4.411

6.  Mechanistic Divergence in the Hydrogenative Synthesis of Furans and Butenolides: Ruthenium Carbenes Formed by gem-Hydrogenation or through Carbophilic Activation of Alkynes.

Authors:  Sebastian Peil; Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-06       Impact factor: 15.336

  6 in total

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