38828-95-4Relevant articles and documents
An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis
Tonogaki, Keisuke,Mori, Miwako
, p. 2235 - 2238 (2002)
Synthesis of 1,3-diene from alkyne and ethylene (1 atm) was improved using ruthenium carbene complex 1b having heterocyclic carbene as a ligand. In this reaction, the heteroatom at the propargylic position was not required, although the reaction of alkyne
A General Nickel-Catalyzed Kumada Vinylation for the Preparation of 2-Substituted 1,3-Dienes
Fiorito, Daniele,Folliet, Sarah,Liu, Yangbin,Mazet, Clément
, p. 1392 - 1398 (2018/02/14)
The identification of two nickel(II) precatalysts for the preparation of 2-substituted 1,3-dienes by a Kumada cross-coupling between vinyl magnesium bromide and vinyl phosphates is described. This is noteworthy as engaging only one vinyl derivative in a transition-metal-catalyzed cross-coupling reaction is already reputedly challenging. Salient features of this method are its operational simplicity, the mild reaction conditions, the low catalyst loadings, the short reaction times, its scalability, and the use of stoichiometric quantities of each coupling partner. The tolerance of the two nickel catalysts to an important number of reactive functional groups and their compatibility with structurally complex molecular architectures has been extensively delineated. A Negishi variant of the reaction has been developed for even more sensitive organic functions such as ester or nitrile. Several other conjugated 1,3-dienes with various substitution patterns have been prepared by combining commercial alkenyl Grignard reagents and/or readily available alkenyl enol phosphates. Proper choice of the nickel catalyst and the reaction temperature gave access to a variety of different olefin isomers with high levels of stereocontrol. Overall, this approach affords conjugated dienes that would not be accessible otherwise and therefore provides a valuable complement to existing methods.
Diversity-oriented synthesis of biaryl derivatives using cross-enyne metathesis, diels-alder reaction, and suzuki-miyaura cross-coupling as key steps
Kotha, Sambasivarao,Seema, Vittal
, p. 2329 - 2334 (2011/10/30)
Biaryl derivatives have been prepared by utilizing cross-enyne metathesis, Diels-Alder reaction followed by aromatization. These biaryl derivatives are further functionalized via Suzuki-Miyaura cross-coupling reaction to generate functionalized terphenyl derivatives. Georg Thieme Verlag Stuttgart - New York.
Regiodiverse three-component synthesis of arenes
Danz, Michael,Hilt, Gerhard
supporting information; experimental part, p. 303 - 308 (2011/04/18)
A ruthenium-catalyzed enyne metathesis reaction followed by a cobalt-catalyzed Diels-Alder reaction and oxidation of the dihydroaromatic intermediate generates the two regioisomeric aromatic products in good overall yields in a one-pot procedure. The regiochemistry of the cycloaddition can be controlled by the ligand choice on the cobalt catalyst to generate the product with the 1,3,5-or the 1,2,4-substitution pattern predominantly. The high functional group tolerance was used to generate bifunctionalized building blocks and finally an unprecedented regioselective Scholl reaction is described.
