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June 14, 2026

Pd-Catalyzed Cyclization and Cyanation of Alkynone O -Methyloximes with tert -Butyl Isocyanide

Key Points

To develop an efficient method for synthesizing polyfunctionalized isoxazoles using palladium catalysis.
Palladium-catalyzed transformation of alkynone O-methyloximes and tert-butyl isocyanide
Examination of substrate compatibility and yield outcomes
Proposed catalytic cycle with trans-oxypalladation and migratory insertion
Broad substrate compatibility achieved with moderate to good yields
Isocyanide proven to be an efficient "CN" source
Diverse nitrile-substituted isoxazoles synthesized from readily available building blocks.

Abstract

A palladium-catalyzed cyclization and cyanation for synthesizing polyfunctionalized isoxazoles derivatives has been disclosed. The commercially available tert -butyl isocyanide has been proved as an efficient “CN” source in this transformation. This new protocol exhibits broad substrate compatibility, leading to diverse nitrile-substituted isoxazoles in moderate to good yields from readily available building blocks alkynone O -methyloximes. A possible catalytic cycle is proposed, involving a tandem sequence of Pd II -initiated trans -oxypalladation, isocyanide migratory insertion, β- tert -butyl elimination.

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