Highly Selective Synthetic Method for 1,6‐Diols Bearing Enyne Functions: Development of 3,6‐Dianion Reagent of 1,2‐Hexadien‐4‐yne Using 1,6‐Dibromo‐2,4‐hexadiyne and Indium

The reaction of aldehydes and ketones with an organoindium reagent generated in situ from indium and 1,6‐dibromo‐2,4‐hexadiyne in the presence of lithium iodide in tetrahydrofuran (THF) selectively produced 1,6‐diols linked to an allenyne unit with complete regioselectivity and chemoselectivity through 1,2‐hexadien‐4‐yn‐3,6‐ylation, indicating that the organoindium acted as the 3,6‐dianion reagent of 1,2‐hexadien‐4‐yne.