Palladium-Catalyzed C-CN activation for intramolecular cyanoesterification of alkynes

Naveen R. Rondla, Samuel M. Levi, Jonathan M. Ryss, Rachel A.Vanden Berg, Christopher J. Douglas

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step.

Original languageEnglish (US)
Pages (from-to)1940-1943
Number of pages4
JournalOrganic Letters
Volume13
Issue number8
DOIs
StatePublished - Apr 15 2011

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