Grubbs Metathesis Ring Closing

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Alkene Metathesis is a technique that only the wisest from the fire nation are capable of mastering. Schindler, who has placed an immense amount of trust in Montgomery, is willing to teach him the art of Alkene Metathesis.

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Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI Paris Tech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, France All articles from this author Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI Paris Tech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, France All articles from this author Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI Paris Tech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, France All articles from this author Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI Paris Tech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, France All articles from this author Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI)-UMR 8231 ESPCI Paris Tech, CNRS, PSL* Research University, 10, rue Vauquelin, 75231 Paris Cedex 05, France All articles from this author Alkenes containing N-heteroaromatics are known to be poor partners in cross-metathesis reactions, probably due to catalyst deactivation caused by the presence of a nitrogen atom.

Metathesis is the formation of a product that has exchanged bonds between starting materials. Alkene metathesis, also known as Olefin metathesis, was the subject of the 2005 Nobel Prize in Chemistry.

The reaction involves the rearrangement of carbon-carbon double bonds, through the use of metal catalysts, such as the Grubbs Ru catalyst, Schrock W, Mo, and Re catalysts, and titanocene-based catalysts. The most commonly accepted mechanism of the Olefin metathesis involves the formation of a metallacyclobutane intermediate, as seen in the below diagram: The Olefin metathesis reaction has very low stereospecificity (although, in some circumstances, the E configuration is preferred).

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The purpose of this mini-review is to give a brief overview of successful metathesis reactions involving olefins containing N-heteroaromatics in order to delineate some guidelines for the use of these challenging substrates in metathesis reactions.

Keywords: Over the past decades, metathesis has become a key reaction within the organic chemist’s toolbox [1-6].

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