Halogen Bond (XB) Promoted α-Tribromomethylation of N-Aryltetrahydroisoquinolines and Further Cyclization to 5,6-Dihydroindolo[2,1-a]isoquinolines.

Abstract

Using CBr4 as a halogen bond donor and the source of tribromomethyl group, a halogen bond promoted tribromomethylation of N-aryltetrahydroisoquinolines was achieved. This reaction was also extended to the construction of the dibenzopyrrocoline alkaloid skeleton through a one-pot process. The mechanistic study confirmed the existence of the halogen bond.