In the presence of dioxygen, an antimony trichloride enabled conjunctive sp3 C-H bond functionalization and carbochlorination of glycines was realized, providing a series of chlorinated quinolines in high yields. The...

A tris(4-bromophenyl)aminium hexachloroantimonate-initiated oxidative Povarov-type reaction between glycines and methylenecyclopropanes was realized in the presence of dioxygen, in which the counterion, SbCl 6 − , served as a chlorine atom donor, enabling the synthesis of a series of chlorinated quinolines in high yields. The mechanistic study showed that the chlorination step might be related to antimony chloride via a radical chlorine atom transfer.

Using CBr 4 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.

A TBN/O2 initiated oxidation of the relatively inert 3,4-C-H bonds of THIQs was accomplished, in which the existence of an α-phosphoric ester group is crucial to enable the dioxygen trapping...

Using tris(4-bromophenyl)aminium hexachloroantimonate as a "waste-utilized"-type initiator, the aerobic oxidation of the sp 3 C−H bond of proline esters was realized via C−H activation relay, giving a series of halogenated pyrroles in high yields. The mechanistic study revealed that the counterion, SbCl 6 − , was involved in the radical chlorination process, which provides a new way to understand the role of the counterions.