Abstract
A one-pot procedure has been developed for the synthesis of substituted naphthalenes from 1-ethynyl-2-alkenylbenzenes. The successive reaction of a variety of 1-ethynyl-2-alkenylbenzenes with BuLi, Et2AlCl, and diisobutylaluminum hydride (DIBAL-H) in one pot gives the corresponding substituted naphthalenes in excellent yields. β, β-Bisaluminated styrenes, which are generated in situ, undergo an intramolecular cyclization reaction to form aluminated naphthalenes. The naphthylaluminum intermediate can be trapped with methanol‑d4 to form the deuterated product, which provides some mechanistic insight. The corresponding iodinated naphthalenes are also obtained on quenching the naphthylaluminum with N-iodosuccinimide (NIS) and iodine.
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