Literature DB >> 27594819

A Ruthenium Catalyst for Olefin Metathesis Featuring an Anti-Bredt N-Heterocyclic Carbene Ligand.

David Martin1, Vanessa M Marx2, Robert H Grubbs2, Guy Bertrand1.   

Abstract

A ruthenium complex bearing an "anti-Bredt" N-heterocyclic carbene was synthesized, characterized and evaluated as a catalyst for olefin metathesis. Good conversions were observed at room temperature for the formation of di- and tri-substituted olefins by ring-closing metathesis. It also allowed for the ring-opening metathesis polymerization of cyclooctadiene, as well as for the cross-metathesis of cis-1,4-diacetoxy-2-butene with allyl-benzene, with enhanced Z/E kinetic selectivity over classical NHC-based catalysts.

Entities:  

Keywords:  olefin metathesis; ruthenium; stable carbenes

Year:  2016        PMID: 27594819      PMCID: PMC5007067          DOI: 10.1002/adsc.201501140

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN: 1615-4150            Impact factor:   5.837


  30 in total

1.  Mechanism and activity of ruthenium olefin metathesis catalysts.

Authors:  M S Sanford; J A Love; R H Grubbs
Journal:  J Am Chem Soc       Date:  2001-07-11       Impact factor: 15.419

Review 2.  Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

Authors:  Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  An air-stable oxyallyl radical cation.

Authors:  David Martin; Curtis E Moore; Arnold L Rheingold; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-29       Impact factor: 15.336

Review 4.  Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

Authors:  Georgios C Vougioukalakis; Robert H Grubbs
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

5.  An N,N'-diamidocarbene: studies in C-H insertion, reversible carbonylation, and transition-metal coordination chemistry.

Authors:  Todd W Hudnall; Christopher W Bielawski
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

6.  Protonolysis of a ruthenium-carbene bond and applications in olefin metathesis.

Authors:  Benjamin K Keitz; Jean Bouffard; Guy Bertrand; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2011-05-16       Impact factor: 15.419

7.  Intramolecular "hydroiminiumation and -amidiniumation" of alkenes: a convenient, flexible, and scalable route to cyclic iminium and imidazolinium salts.

Authors:  Rodolphe Jazzar; Jean-Baptiste Bourg; Rian D Dewhurst; Bruno Donnadieu; Guy Bertrand
Journal:  J Org Chem       Date:  2007-04-05       Impact factor: 4.354

8.  Kinetic Selectivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes.

Authors:  Donde R Anderson; Thay Ung; Garik Mkrtumyan; Guy Bertrand; Robert H Grubbs; Yann Schrodi
Journal:  Organometallics       Date:  2008-01-12       Impact factor: 3.876

9.  31P NMR chemical shifts of carbene-phosphinidene adducts as an indicator of the π-accepting properties of carbenes.

Authors:  Olivier Back; Martin Henry-Ellinger; Caleb D Martin; David Martin; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-31       Impact factor: 15.336

10.  A cyclic diaminocarbene with a pyramidalized nitrogen atom: a stable N-heterocyclic carbene with enhanced electrophilicity.

Authors:  David Martin; Nicolas Lassauque; Bruno Donnadieu; Guy Bertrand
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-08       Impact factor: 15.336

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