Abstract
Construction of carbon–carbon bonds is one of the most important tools for the synthesis of complex organic molecules. Among multiple possibilities are the carbonyl–alkyne and carbonyl–olefin metathesis reactions, which are used to form new carbon–carbon bonds between carbonyl derivatives and unsaturated organic compounds. As many different approaches have already been established and offer reliable access to C=C bond formation via carbonyl–alkyne and carbonyl–olefin metathesis, focus is now shifting towards cost efficiency, sustainability and environmentally friendly metal catalysts. Iron, which is earth-abundant and considered as an eco-friendly and inexpensive option in comparison to traditional metal catalysts, fulfils these requirements. Hence, the focus of this review is on recent advances in the iron-catalyzed carbonyl–alkyne, carbonyl–olefin and related C–O/C–O metathesis reactions. The still large research potential for ecologically and economically attractive and sustainable iron-based catalysts is demonstrated.
Highlights
The formation of carbon–carbon bonds is one of the most important goals in chemistry [1].For fast, efficient and selective coupling, catalysis via metal salts or metal complexes is an elegant option with versatile applications in academic research or industry [2,3,4]
As many different approaches have already been established and offer reliable access to C=C bond formation via carbonyl–alkyne and carbonyl–olefin metathesis, focus is shifting towards cost efficiency, sustainability and environmentally friendly metal catalysts
In contrast previously iron(III)chloride, bindsmodification to the carbonyls without an electron transfer event, towhile small reported carbonyl–olefin metathesis reactions, two additional side-paths occur during the reaction, impurities or usage of iron(III)chloride hydrate did not affect the yield of the metathesis reaction
Summary
The formation of carbon–carbon bonds is one of the most important goals in chemistry [1]. One of the most important methodologies is the metal-catalyzed olefin–olefin metathesis reaction (Scheme 1a), which is a powerful tool for the formation of carbon–carbon double bonds with a wide range of applications [9,10,11,12]. A special case is the C–O/C–O metathesis reaction (as depicted in Scheme 1d), which forms a new. Even though the reaction does not form a new C–C bond, the reaction can be considered as a ring-closing C–O/C–O metathesis of aliphatic ethers [18]. A special case is the C–O/C–O metathesis reaction (as depicted in Scheme 1d), which forms a new C–O bond resulting in cyclic ether derivatives. C–C bond, the reaction can be considered as a ring-closing C–O/C–O metathesis of aliphatic ethers [18].
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