Catalytic Activation of Olefins by Metal Triflates and Triflimides: Application to Fragrance Chemistry

Abstract

Fragrance compounds constitute a wide family of relatively volatile compounds presenting interesting odour properties. Several processes catalysed by metal triflates and triflimides have been recently developed with a view to applications to fragrance chemistry. These reactions, involving the activation of non-activated olefins, mainly involve inter- and intramolecular carbon-carbon, carbon-oxygen and carbon-sulfur bond formation.

Silver‐Free Two‐Component Approach in Gold Catalysis: Activation of [LAuCl] Complexes with Derivatives of Copper, Zinc, Indium, Bismuth, and Other Lewis Acids

“…As mentioned above (see Table 1, entry 6), the transformation of 1 a into 2 a could be carried out in toluene at 110 °C by using 0.1 mol % [(JohnPhos)AuCl] ( A ) and 10 mol % Cu(OTf) 2 . The Lewis acids displayed in Table 5 were tested in the absence of gold at 110 °C, which showed that Ga(OTf) 3 , Al(OTf) 3 , Bi(OTf) 3 , and especially In(OTf) 3 are potent catalysts (see conversions in parentheses, 12, 16, 38, and 77 % respectively) 30–32. On the other hand, at 50 °C, none of these Lewis acids promoted the transformation of 1 a into 2 a .…”

Water-Tolerant Trifloaluminate Ionic Liquids: New and Unique Lewis Acidic Catalysts for the Synthesis of Chromane

“…Kobayashi and co-workers found that certain Lewis acidic metal triflates (M = Al, Ga, Ln) are stable in aqueous media (Kobayashi and Manabe, 2000 ; Kobayashi et al, 2002 ). Following this, such metal triflates were reported as water-tolerant Lewis acidic catalysts for a range of organic transformations: aldol condensations, Diels-Alder reactions, Friedel-Crafts acylations and alkylations, radical additions, aromatic nitrations and sulfonylations (Lub et al, 2005 ; Coulombel et al, 2009 ; Robertson and Wu, 2010 ; Williams and Lawton, 2010 ; Prakash et al, 2012 ; Lemière and Duñach, 2013 ; Markiton et al, 2018 ). The metal triflate catalysts were active at low concentrations, bearing the promise of cost-effective and efficient processes, but suffered from limitations in solubility.…”

Synthesis and olfactory evaluation of allylic α‐quaternary ether ketones

“…In this context, our group's research is focused on the development of new catalytic methodologies for the formation of intramolecular carbon–carbon and carbon–oxygen bonds. This chemistry aims for the synthesis of low‐molecular‐weight compounds with a potential utility as flavour and fragrance ingredients . Special attention is hereby given to the scalability, robustness, and operational simplicity of the experimental procedure.…”