Application of Olefin Metathesis in the Synthesis of Carbo- and Heteroaromatic Compounds—Recent Advances

Abstract

The olefin metathesis reaction has found numerous applications in organic synthesis. This is due to a number of advantages, such as the tolerance of most functional groups and sterically demanding olefins. This article reviews recent advances in the application of the metathesis reaction, particularly the metathetic cyclization of dienes and enynes, in synthesis protocols leading to (hetero)aromatic compounds.

Triazenolysis of Alkenes: Aza-version of Ozonolysis

“…This observation pointed to the importance of stabilizing BH 3 , formed during the reaction, by ethereal solvents (vide infra). Additionally, varying the temperature showed similar e cacy of re ux and 90 °C (entries 2 and 10), whereas lower temperatures led to inferior results (entries [11][12]. Reducing the amount of NaBH 4 did not improve the outcome of the process (entry 13).…”

“…Those transformations have demonstrated their applicability in the synthesis of myriad of organic compounds, signi cantly propelling approaches for the preparation of pharmaceuticals, 6-8 materials [9][10][11] and agrochemicals. 12,13 The groundbreaking example of such reactivity was highlighted by the 2005 Nobel Prize for the development of ole n metathesis, which allows a construction of new C = C motif by metal-catalyzed cleavage of two starting C = C units (Fig. 1A).…”

Magnetic Thiaminum Octamolybdate Nanocatalyst for Oxygenation of Styrenes to Benzaldehydes and Tandem Synthesis of Benzimidazoles

“…The widespread applications of styrenes as readily available and nonactivated aromatic terminal olefins in important reactions such as Heck reaction, olefin hydroformylation, Wacker process, olefin metathesis, and synthesis of alkylthio-substituted 1,4-enediones demonstrate their importance in synthetic organic chemistry.…”

Tuning the Latency by Anionic Ligand Exchange in Ruthenium Benzylidene Phosphite Complexes

“…Although ruthenium olefin metathesis catalysts have been intensively studied and are known for their excellent reactivity, this research field is quite popular, mainly because it offers a reliable, adaptable synthetic tool for both commercial and academic applications and because there are still challenges to be met, both in the selectivity and longevity of the catalysts. Accordingly, the efficiency and selectivity of ruthenium catalysts for olefin metathesis processes have been significantly improved by fine-tuning the ruthenium framework (ligand sphere) [10][11][12]. Among these, metathesis processes have been significantly improved by fine-tuning the ruthenium framework (ligand sphere) [10][11][12].…”

“…Accordingly, the efficiency and selectivity of ruthenium catalysts for olefin metathesis processes have been significantly improved by fine-tuning the ruthenium framework (ligand sphere) [10][11][12]. Among these, metathesis processes have been significantly improved by fine-tuning the ruthenium framework (ligand sphere) [10][11][12]. Among these, ruthenium phosphite complexes have received much interest due to their high activity and stability [13][14][15][16][17][18].…”