Pd-catalyzed allylic amination in supercritical carbon dioxide: Synthesis of carborane-containing terpenoids

Pd-catalyzed amination of allylic carbonates with N-(ortho-carboran-3-yl)-N-methylamine was carried out in supercritical CO2. It has been demonstrated that complete conversion of allylic carbonates to the corresponding carborane amines with excellent regioselectivity may be achieved in scCO2 (170 atm, 60 °C) using NaHCO3 as the acceptor base. The reaction offers a selective method for the preparation of allylic amines and provides a useful approach to new terpenoids.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide