Ball-Milling-Enabled Nickel-Catalyzed Reductive 1,4-Alkylarylation of 1,3-Enynes under an Air Atmosphere.

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