Ene-Allenes: Access from Dialkynes by an Intramolecular anti-Carbopalladation Cascade
Pedram Kalvani, Catherine Vanbel, Heinrich F. von Köller, Daniel B. Werz
TL;DR
A new palladium-catalyzed reaction creates complex ene-allenes from dialkynes, forming multiple carbon-carbon bonds efficiently.
Contribution
A novel intramolecular palladium-catalyzed cascade combining anti- and syn-carbopalladation is introduced for ene-allene synthesis.
Findings
The cascade reaction forms two new carbon–carbon bonds across the first double bond.
The process terminates via β-hydride elimination from a vinyl Pd(II) complex.
Diverse ene-allenes in oligo(hetero)cyclic systems are synthesized with up to 73% yield.
Abstract
Herein, an intramolecular palladium-catalyzed cascade reaction is reported consisting of both formal anti-carbopalladation and syn-carbopalladation of internal alkynes. This process leads to two new carbon–carbon bonds across the first double bond formed. The cascade is terminated by β-hydride elimination from the emerging vinyl Pd(II) complex. As a result, di-, tri-, and tetrasubstituted ene-allenes embedded in an oligo(hetero)cyclic ring system are synthesized in yields of up to 73%.
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Catalytic Alkyne Reactions · Catalytic Cross-Coupling Reactions