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Updated: Jun 12, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Streamlined synthesis of functionalized dibenzo[a,e]pentalenes through potassium-mediated cyclization and late-stage
Marcell M Bogner1, Bence Sóvári1, Péter P Kalapos1
1Institute of Organic Chemistry, HUN-REN Research Centre for Natural Sciences 1117 Budapest Hungary london.gabor@ttk.hu.
Abstract:
Herein we report a simple and scalable synthetic platform for the dibenzo[a,e]pentalene (DBP) framework. Via potassium-mediated cyclization of TIPS-protected phenylacetylene we were able to produce multi-decagram-scale (>25 g) quantities of a 5,10-TIPS protected DBP key intermediate, which enabled further complexity-enhancing transformations. Halodesilylations on the pentalene core and aryl thianthrenation on the annulated benzene rings enabled highly modular synthetic pathways towards complex DBP-based structures.
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