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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Related Experiment Video

Updated: Jul 17, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

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Access to Functionalized Isocoumarin Via Palladium-Catalyzed Tandem Heck Cyclization/Lactonization.

Hongbo Qi1, Zhipeng Li1, Wen-Cong Li1,2

  • 1Inner Mongolia Key Laboratory of Synthesis and Application of Organic Functional Molecules, Department of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, China.

Organic Letters
|July 16, 2026
PubMed
Summary

A novel palladium-catalyzed reaction efficiently creates functionalized isocoumarins via tandem Heck cyclization and lactonization. This single-step process forms four bonds, streamlining synthesis and offering new routes to valuable compounds.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Isocoumarins are important structural motifs found in numerous natural products and pharmaceuticals.
  • Efficient synthetic routes for constructing functionalized isocoumarins are highly sought after in medicinal chemistry and drug discovery.
  • Palladium-catalyzed reactions, such as the Heck reaction, are powerful tools for carbon-carbon bond formation.

Purpose of the Study:

  • To develop a novel, efficient, and single-step method for synthesizing functionalized isocoumarins.
  • To explore a palladium-catalyzed tandem Heck cyclization/lactonization reaction sequence.
  • To elucidate the mechanistic pathway of the developed tandem reaction.

Main Methods:

  • Utilized a palladium catalyst to promote a tandem Heck cyclization followed by lactonization.
  • Employed aryl iodide substrates and an alkyne component in the reaction system.
  • Conducted mechanistic studies involving isotopic labeling and control experiments to understand the reaction pathway.

Main Results:

  • Successfully synthesized a range of functionalized isocoumarins in a single operation.
  • The tandem reaction efficiently formed two carbon-oxygen and two carbon-carbon bonds.
  • Mechanistic investigations revealed that water or base acts as the oxygen source, and the aryl iodide functions as both a coupling partner and an oxidant.

Conclusions:

  • The developed palladium-catalyzed tandem Heck cyclization/lactonization reaction provides an efficient strategy for isocoumarin synthesis.
  • This methodology offers a streamlined approach, forming multiple bonds in one pot.
  • The mechanistic insights provide a foundation for further optimization and application of this reaction in organic synthesis.