Construction of Hexahydrophenanthrenes By Rhodium(I)‐Catalyzed Cycloisomerization of Benzylallene‐Substituted Internal Alkynes through C−H Activation

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Abstract
The treatment of benzylallene‐substituted internal alkynes with [RhCl(CO)2]2 effects a novel cycloisomerization by C(sp2)−H bond activation to produce hexahydrophenanthrene derivatives. The reaction likely proceeds through consecutive formation of a rhodabicyclo[4.3.0] intermediate, σ‐bond metathesis between the C(sp2)−H bond on the benzene ring and the C(sp2)−RhIII bond, and isomerization between three σ‐, π‐, and σ‐allylrhodium(III) species, which was proposed based on experiments with deuterated substrates.
Funding Information
  • JSPS
  • KAKENHI (15H02490, 15K18826)

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