91352-20-4Relevant academic research and scientific papers
Iodine-Catalyzed Nazarov Cyclizations
Koenig, Jonas J.,Arndt, Thiemo,Gildemeister, Nora,Neud?rfl, J?rg-M.,Breugst, Martin
, p. 7587 - 7605 (2019/06/27)
The Nazarov cyclization is an important pericyclic reaction that allows the synthesis of substituted cyclopentenones. We now demonstrate that this reaction can be performed under very mild, metal-free reaction conditions using molecular iodine as the catalyst. A variety of different divinyl ketones including aromatic systems undergo the iodine-catalyzed reaction with moderate to very good yields in both polar and apolar solvents. Our mechanistic studies indicate that the Nazarov system is activated through a halogen bond between the carbonyl group and the catalyst, and other modes of action like Br?nsted acid or iodonium ion catalysis are unlikely. Furthermore, addition of iodine to the double bond or a putative iodine-catalyzed cis-trans isomerization of the employed olefins seem not to be an important side reaction here.
A mild, catalytic and efficient Nazarov cyclization mediated by phosphomolybdic acid
Murugan, Kaliyappan,Srimurugan, Sankareswaran,Chen, Chinpiao
supporting information; experimental part, p. 1127 - 1129 (2010/06/18)
A mild, selective and efficient Nazarov cyclization of divinyl ketones catalyzed by phosphomolybdic acid (PMA) is described. The process demonstrates a broad substrate scope with functional group tolerance under short reaction times. PMA supported on silica gel is more efficient than the bulk catalyst and is recycled up to three times without significant activity loss.
Catalytic enantioselective 1,3-dipolar cycloadditions of alkyl diazoacetates with α,β-disubstituted acroleins
Gao, Lizhu,Hwang, Geum-Sook,Lee, Mi Young,Ryu, Do Hyun
supporting information; experimental part, p. 5460 - 5462 (2009/12/08)
A catalytic route to highly functionalized chiral 2-pyrazolines by an asymmetric 1,3-dipolar cycloaddition reaction of ethyl diazoacetate with α-substituted and α,β-disubstituted acroleins has been developed; in the presence of chiral (S)-oxazaborolidiniu
