jo501890z_si_001.pdf (6.8 MB)
Redox and Lewis Acid Relay Catalysis: A Titanocene/Zinc Catalytic Platform in the Development of Multicomponent Coupling Reactions
journal contribution
posted on 2014-12-19, 00:00 authored by Joseph
B. Gianino, Catherine A. Campos, Antonio J. Lepore, David M. Pinkerton, Brandon L. AshfeldA titanocene-catalyzed
multicomponent coupling is described herein.
Using catalytic titanocene, phosphine, and zinc dust, zinc acetylides
can be generated from the corresponding iodoalkynes to affect sequential
nucleophilic additions to aromatic aldehydes. The intermediate propargylic
alkoxides are trapped in situ with acetic anhydride,
which are susceptible to a second nucleophilic displacement upon treatment
with a variety of electron-rich species, including acetylides, allyl
silanes, electron-rich aromatics, silyl enol ethers, and silyl ketene
acetals. Additionally, employing cyclopropane carboxaldehydes led
to ring-opened products resulting from iodine incorporation. Taken
together, these results form the basis for a new mode of three-component
coupling reactions, which allows for rapid access to value added products
in a single synthetic operation.
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Catalyticmulticomponentzinc dustPlatformcyclopropane carboxaldehydesRedoxzinc acetylidesiodine incorporationspeciesvarietysilyl enol ethersacetic anhydridearomaticaccesstitanoceneRelay Catalysisphosphinepropargylic alkoxidesallyl silanessequential nucleophilic additionsnucleophilic displacementsilyl ketene acetalsresults formLewisbasisiodoalkyneMulticomponentTitanoceneReactionsAmode
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