Rate Enhanced Olefin Cross-Metathesis Reactions: The Copper Iodide Effect

Abstract

Copper iodide has been shown to be an effective co-catalyst for the olefin cross metathesis reaction. In particular, it has both a catalyst stabilizing effect due to iodide ion, as well as copper(I)-based phosphine-scavenging properties that apply to use of the Grubbs-2 catalyst. A variety of Michael acceptors and olefinic partners can be cross-coupled under mild conditions in refluxing diethyl ether that avoid chlorinated solvents. This effect has also been applied to chemistry in water at room temperature using the new surfactant TPGS-750-M.

Recycling Mitsunobu coupling: a shortcut for troublesome esterifications

“…12 As the separation of Z and E-alkenes proved to be difficult in certain cases, we decided to directly hydrogenate the crude mixture in a one-pot sequence (Scheme 4).…”

Synthesis of Novel Fatty Substituted 4-methyl-2HChromen-2-one via Cross Metathesis: Potential Antioxidants and Chemotherapeutic Agents

“…Fatty acids are also known to play a very important role in the synthesis of a number of oleochemicals with industrial and biological applications 39 . Also, there exists no reports on the synthesis of glycosidic and fatty acid derivatives of coumarins and hence with this background an attempt was made to synthesize hydroxyl, benzyl, glycosidic and fatty acid derivatives of 7-allyloxy -4-methyl-2H-chromen-2-one employing conventional method followed by cross metathesis in presence of CuI 40 .…”

Practical Preparation of (4R,5R,E)-methyl 5-(tert-butyldimethylsilyloxy)-4-hydroxyhepta-2,6-dienoate

“…For example, shorter reaction time and better yields were achieved by applying microwave irradiation [6,7,8]. One interesting approach was reported by Lipshutz's group: they found that copper (I) iodide is an effective additive for olefin cross-metathesis reactions [9]. Thus, a variety of Michael acceptors or electron deficient olefins can be cross-coupled under mild reaction conditions and environmentally benign solvents, such as ethers, can be used, rather than chlorinated solvents.…”

“…by applying microwave irradiation and strategy developed by Voigtritter et al [9]. The conventional procedure [3] was also included for comparison.…”