A method for synthesizing a full carbon quaternary carbon cyclic ketone spirocyclic pseudoindole derivative

By utilizing the synergistic effect of the carbonyl metal compound Co2(CO)8 and the palladium catalyst, carbonyl introduction and spirocyclic construction can be completed in one step, solving the synthetic problem of all-carbon quaternary carbocyclic ketone spirocyclic pseudoindole derivatives. This method is safe and efficient and applicable to multifunctional compounds.

CN116813528BActive Publication Date: 2026-02-27JIANGSU OCEAN UNIV
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Patent Information

Application Number
CN202310790925.X
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-06-30
Publication Date
2026-02-27
Estimated Expiration
2043-06-30

AI Technical Summary

Technical Problem

Existing technologies make it difficult to efficiently synthesize all-carbon quaternary carbocyclic ketone spirocyclic pseudoindole derivatives, especially due to the stepwise difficulty in introducing the carbonyl group and constructing the spirocycle. Furthermore, the use of highly toxic carbon monoxide gas does not conform to the principles of green chemistry.

Method used

Using the carbonyl metal compound Co2(CO)8 as a safe carbonyl source, combined with a palladium catalyst and a phosphine ligand, the carbonyl group was introduced and the spirocyclic ring was constructed in one step through oxidative addition, CO migration insertion and dearomatization processes, and a multifunctional all-carbon quaternary carbon cyclic ketone spirocyclic pseudoindole derivative was synthesized in a one-pot method.

Benefits of technology

A safe and efficient synthesis of all-carbon quaternary carbon cyclic ketone spirocyclic pseudoindole derivatives was achieved, avoiding the use of highly toxic gases. The operation is simple, has broad functional group compatibility, high yield, mild reaction conditions, and few byproducts.

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Abstract

This invention discloses a method for synthesizing a full-carbon quaternary carbocyclic ketone-spirocyclic pseudoindole derivative. This method uses a metal carbonyl compound as a safe carbonyl source and involves a catalytic cycle from zero-valent palladium to divalent palladium. Specifically, it involves the oxidative addition of palladium(O) via a carbon-halogen bond, the coordination and migration insertion of CO to form a carbonyl palladium species, followed by nucleophilic attack of the indole C3 ring to achieve dearomatization of the indole ring, and then reductive elimination to obtain the full-carbon quaternary carbocyclic ketone-spirocyclic pseudoindole derivative. Specifically, compound 1 and the metal carbonyl compound Co2(CO)8 are reacted under heating conditions with palladium as a catalyst, organophosphine as a ligand, and sodium salt as a base to obtain the full-carbon quaternary carbocyclic ketone-spirocyclic pseudoindole molecule. This method is a novel synthetic method for full-carbon quaternary carbocyclic ketone-spirocyclic pseudoindole derivatives, solving the problems of existing technologies such as the need for multiple reaction steps, harsh reaction conditions, narrow substrate range, and high toxicity of starting materials.
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