Formation and Cycloaddition Reactions of a Reactive Boraalkene Stabilized Internally by N-Heterocyclic Carbene

The synthesis of element-carbon double bonds is of great importance for the development and understanding of reactive pi-bonded systems in chemistry. The seven-membered heterocyclic system 4 b is readily made by internal C-H activation at a pendent isopropyl methyl group of the respective [(IPr)C6F5BH](+) borenium ion. Subsequent deprotonation with the IMes carbene gives the neutral cyclic boraalkene system 5 b. The B=C double bond in compound 5 b adds carbon dioxide, CS2, sulfur dioxide, phenyl isocyanate, an acetylenic ester or two NO molecules to give the corresponding four-membered ring annulated heterocycles. With sulfur or selenium 5 b gives the respective three-membered ring systems. N2O reacts with 5 b to give a mixture of the related oxaborirane 18 and a unique [B]OH containing diazoalkane product 19.

Automated summary

The synthesis of element-carbon double bonds is described in this passage, focusing on the reactions with various molecules to form annulated heterocycles.