Grubbs Metathesis Ring Closing

Various approaches have been explored to allow the use of primary and secondary amines in ring-closing metathesis (RCM) and cross-metathesis (CM), and one of them is the transformation of amines into carbamates, amides or sulfonamides [27-29].As an alternative, metathesis reactions can be performed with olefins possessing ammonium salts that can be formed from the corresponding amines either in a preliminary step or in situ, in the presence of an acidic additive [30-35].

Various approaches have been explored to allow the use of primary and secondary amines in ring-closing metathesis (RCM) and cross-metathesis (CM), and one of them is the transformation of amines into carbamates, amides or sulfonamides [27-29].As an alternative, metathesis reactions can be performed with olefins possessing ammonium salts that can be formed from the corresponding amines either in a preliminary step or in situ, in the presence of an acidic additive [30-35].

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In this review, we would like to give an overview of successful metatheses involving alkenes that possess N-heteroaromatics in order to delineate some guidelines.

Some mechanistic insights dealing with catalyst deactivation caused by amino derivatives will be first presented and discussed.

However, some examples of ring-closing and cross-metathesis involving alkenes that incorporate N-heteroaromatics can be found in the literature.

In addition, recent mechanistic studies have focused on the rationalization of nitrogen-induced catalysts deactivation.

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For further information, including about cookie settings, please read our Cookie Policy .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].In addition, Lewis acids in catalytic amounts were shown to enhance the reactivity of amino compounds in metathesis reactions [36,37].Involvement of N-heteroaromatics containing olefins in metathesis has been less documented.The Schrock catalyst was commercialized in 1990 and is molybdenum(IV)- and tungsten(IV)-based while the Grubbs catalyst (first generation) was published in 1992 and makes use of ruthenium(II) carbenoid complexes.In 1999 a second generation Grubbs catalyst was developed that is stable when exposed to moisture and air with an effectiveness 100 to 1000 times that of the first generation.By continuing to use this site, you consent to the use of cookies.We use cookies to offer you a better experience, personalize content, tailor advertising, provide social media features, and better understand the use of our services.Ring-opening metathesis polymerization (ROMP): Ring opening of strained cyclic olefin to give open chain metal carbene provides driving force for ROM.A general mechanism for the ROMP can be seen below: Ring Opening Metathesis requires a strained ring to proceed. An example reaction of a ROMP reaction can be seen below: The Grubbs and Schrock catalysts were developed independently in the 1990s.