5466-77-3Relevant articles and documents
Cross metathesis with acrylates: N-heterocyclic carbene (NHC)- versus cyclic alkyl amino carbene (CAAC)-based ruthenium catalysts, an unanticipated influence of the carbene type on efficiency and selectivity of the reaction
Kaczanowska, Katarzyna,Trzaskowski, Bartosz,Peszczyńska, Aleksandra,Tracz, Andrzej,Gawin, Rafa?,Olszewski, Tomasz K.,Skowerski, Krzysztof
, p. 6366 - 6374 (2020)
Olefin metathesis has been widely explored as a handle for chemical diversification, a feature critical across chemical sectors. Cross metathesis (CM) with acrylic acid derivatives is an example of important but, due to the low catalyst's efficiency, industrially non-utilized transformation. Here we report on systematic evaluation of ruthenium-based catalysts bearing N-heterocyclic carbene (NHC) or cyclic alkyl amino carbene (CAAC) ligands in cross metathesis with methyl acrylate. Dramatic influence of the carbene type on the reaction's efficiency and selectivity has been found. Density functional theory (DFT) calculations suggest that the kinetic selectivity is the main factor differentiating NHC- and CAAC-based ruthenium complexes. Productive turnover number (TON) of 49 900 at 10 ppm loading of nitro-substituted Hoveyda-Grubbs complex (nitro-Grela catalyst) was obtained in the studied reaction, representing the highest efficiency reported to date for this transformation. High efficiency and selectivity of nitro-Grela catalyst was then utilized in cross metathesis of trans-anethole with 2-ethylhexyl acrylate to efficiently produce octyl methoxycinnamate (86 % yield), an antioxidant used in sunscreen formulations.
Method for catalytically synthesizing isooctyl p-methoxycinnamate
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Paragraph 0022-0027, (2020/01/14)
The invention discloses a method for catalytic synthesis of isooctyl p-methoxycinnamate, which comprises the following steps: reacting p-methoxycinnamic acid and isooctyl alcohol which are used as rawmaterials in the presence of a solid acid catalyst for 2-6 hours to synthesize isooctyl p-methoxycinnamate. According to the method, isooctyl p-methoxycinnamate and isooctyl alcohol are used as raw materials, the catalyst is solid acid, and the method has the characteristics of mild reaction conditions, simple equipment and the like, and has a good practical application prospect.
Mimics of Pincer Ligands: An Accessible Phosphine-Free N-(Pyrimidin-2-yl)-1,2-azole-3-carboxamide Framework for Binuclear Pd(II) Complexes and High-Turnover Catalysis in Water
Bumagin, Nikolay A.,Dikusar, Evgenij A.,Ivashkevich, Ludmila S.,Kletskov, Alexey V.,Kolesnik, Iryna A.,Lyakhov, Alexander S.,Petkevich, Sergey K.,Potkin, Vladimir I.
supporting information, (2020/08/12)
We report for the first time cyclic phosphine-free "head to tail"N,N,N pincer-like (pincer complexes mimicking) N-(pyrimidin-2-yl)-1,2-azole-3-carboxamide Pd(II) complexes with deprotonated amide groups as high-turnover catalysts (TON up to 106, TOF up to 1.2 × 107 h-1) for cross-coupling reactions on the background of up to quantitative yields under Green Chemistry conditions. The potency of the described catalyst family representatives was demonstrated in Suzuki-Miyaura, Mizoroki-Heck, and Sonogashira reactions on industrially practical examples. Corresponding ligands could be synthesized based on readily available reagents through simple chemical transformations. Within the complex structures, a highly unusual 1,3,5,7-tetraza-2,6-dipalladocane frame could be observed.