Efficient Palladium‐Catalyzed Aerobic Oxidative Carbocyclization to Seven‐Membered Heterocycles.

Liu, Jie; Bäckvall, Jan‐E.

The use of molecular oxygen in palladium‐catalyzed oxidation reactions is highly widespread in organic chemistry. However, the direct reoxidation of palladium by O2 is often kinetically unfavored, thus leading the deactivation of the palladium catalyst during the catalytic cycle. In the present work, we report a highly selective palladium‐catalyzed carbocyclization of bisallenes to seven‐membered heterocycles under atmospheric pressure of O2. The use of a homogenous hybrid catalyst (Co(salophen)‐HQ, HQ=hydroquinone) significantly promotes efficient electron transfer between the palladium catalyst and O2 through a low‐energy pathway. This aerobic oxidative transformation shows broad substrate scope and functional group compatibility and allowed the preparation of O‐containing seven‐membered rings in good yields in most cases.

ORGANIC chemistry; HETEROCYCLIC compounds; CHARGE exchange; ATMOSPHERIC pressure; CATALYSTS; HYDROQUINONE; CATALYST poisoning; PALLADIUM catalysts

Chemistry - A European Journal, 2020, Vol 26, Issue 67, p15513

0947-6539

Academic Journal

10.1002/chem.202004265