63353-48-0Relevant academic research and scientific papers
Copper-catalyzed [1,2]-rearrangements of allylic iodides and aryl α-diazoacetates
Xu, Bin,Gartman, Jackson A.,Tambar, Uttam K.
, p. 4150 - 4159 (2017)
The [1,2]- and [2,3]-rearrangements of iodonium ylides are synthetically useful reactions for the generation of functionalized α-iodoesters. Allylic iodides are coupled with α-diazoesters in the presence of a copper catalyst and a ligand to generate iodonium ylides, which undergo metal-mediated rearrangements. By fine-tuning the structure of the ligand, we have reversed the regioselectivity of copper-catalyzed reactions of iodonium ylides from [2,3]- to [1,2]-rearrangements with the use of alternate bipyridine ligands. The preference for [1,2]-rearrangements was further improved by using bulky aryl α-diazoester substrates. Several α-iodoesters with a diverse range of functional groups were generated in good yields (up to 88% yield) and high regioselectivities (up to >95:5 regioisomeric ratio). A deuterium-labeled substrate was utilized to gain insight into the mechanism of the reaction.
Cycloadditions, 12. - Influence of Aromatic Alkyl Groups on the Intramolecular Diels-Alder Reaction of Aryl Allenecarboxylates and of Allenecarboxanilides
Himbert, Gerhard,Fink, Dieter,Diehl, Klaus
, p. 431 - 442 (2007/10/02)
The aryl allenecarboxylates 4a-o and the allenecarboxanilides 9a, b, e, h, and l, which differ from one another only by the number or by the size of the alkyl groups attached to the arene, are synthesized by the ylide method via the appropriately substituted 2-halo-, 2-phosphonio-, and 2-phosphoranylideneacetic acid derivatives (1-->2-->3-->4 and 6-->7-->8-->9, resp.).By refluxing in xylene they are transformed into the tricyclic compounds 5 and 10; the rates and their differences are discussed.
