N-Heterocyclic Carbene Boranes are Hydrogen Donors in Masamune-Bergman Reactions of Benzo[3,4]cyclodec-3-ene-1,5-diynes.

ABSTRACT

Thermal reactions of benzo[3,4]cyclodec-3-ene-1,5-diyne with N-heterocyclic carbene boranes (NHC-boranes) provided mixtures of 9-borylated 1,2,3,4-tetrahydroanthracenes along with 1,2,3,4-tetrahydroanthracene. These products indicate that NHC-boranes serve as hydrogen donors to a p-benzyne intermediate formed by the Masamune-Bergman reaction. Experimental results support a radical mechanism in nonpolar solvents, but suggest that ionic mechanisms compete in the production of 1,2,3,4-tetrahydroanthracene when the reaction is performed in a polar solvent.