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Updated: Jun 6, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Radical cyclizations terminated by Ir-catalyzed hydrogen atom transfer
Andreas Gansäuer1, Matthias Otte, Lei Shi
1Kekulé-Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard Domagk Strasse 1, 53121 Bonn, Germany. andreas.gansaeuer@uni-bonn.de
A novel system couples radical cyclization with iridium-catalyzed hydrogen atom transfer (HAT). Vaska's complex efficiently activates H(2) for this catalytic process.
Area of Science:
- Organic Chemistry
- Catalysis
- Reaction Mechanisms
Background:
- Radical cyclization is a powerful tool in organic synthesis.
- Hydrogen atom transfer (HAT) is crucial for many catalytic processes.
- Developing efficient and selective catalytic systems remains a key challenge.
Purpose of the Study:
- To describe a new system coupling catalytic radical cyclization and Ir-catalyzed hydrogen atom transfer (HAT).
- To identify a suitable HAT catalyst that rapidly activates H(2) without causing hydrogenation.
- To demonstrate the efficiency of Vaska's complex in this dual catalytic system.
Main Methods:
- Utilizing a system that combines radical cyclization with Ir-catalyzed HAT.
- Screening and evaluating potential HAT catalysts for H(2) activation.
- Characterizing the performance of Vaska's complex as the HAT catalyst.
Main Results:
- A successful coupling of catalytic radical cyclization and Ir-catalyzed HAT was achieved.
- Vaska's complex was identified as an efficient HAT catalyst, activating H(2) rapidly.
- The catalyst did not promote undesired hydrogenation reactions.
Conclusions:
- The described system provides an effective method for combining radical cyclization and HAT catalysis.
- Vaska's complex is a suitable catalyst for Ir-catalyzed HAT, offering rapid H(2) activation.
- This work expands the toolkit for catalytic radical reactions.
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