Ball-Milling-Enabled\nNickel-Catalyzed Reductive 1,4-Alkylarylation\nof 1,3-Enynes under an Air Atmosphere

A ball-mill-enabled nickel-catalyzed 1,4-alkylarylation\nof 1,3-enynes\nwith organic bromides has been developed, offering a versatile method\nfor assembling tetrasubstituted allenes. This approach, the first\nof ball-milling-based remote radical coupling, overcomes the limitations\nof traditional solution-phase methods, such as the need for air- and\nmoisture-sensitive reagents, the use of bulk solvents, and prolonged\nreaction times. Given the outstanding performance of ball-milling-based\nradical reduction coupling reactions, we anticipate further advancements\nin sustainable and efficient synthetic methodologies.