A palladium‐catalyzed double consecutive C(alkenyl)–H activation/alkyne insertion method utilizing a free carboxylic acid as a directing group in the preparation of functionalized naphthalenes is reported. The reaction mechanism involves a sequence of the C (alkenyl)−H activation/alkyne insertion/1,4‐palladium migration/reductive elimination steps. The second alkyne insertion occurred at the phenyl ring of the intermediate generated from the first alkyne insertion via 1,4‐palladium migration, which is an uncommon case in typical C–H activation/alkyne insertion chemistry, providing functionalized naphthalene products. Additionally, the kinetic studies and control experiments as well as density functional theory (DFT) studies are also investigated to elucidate the reaction mechanism.

中文翻译：

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通过 C（烯基）-H 活化/双炔烃插入/1,4-Pd 迁移的羧酸盐定向氧化环化：官能化萘的合成


报道了一种钯催化的双连续 C（烯基）-H 活化/炔烃插入方法，该方法利用游离羧酸作为定向基团制备官能化萘。反应机理涉及一系列 C（烯基）-H 活化/炔烃插入/1,4-钯迁移/还原消除步骤。第二次炔烃插入发生在第一次炔烃插入通过 1,4-钯迁移产生的中间体的苯环处，这在典型的 C-H 活化/炔烃插入化学中并不常见，提供官能化萘产物。此外，还研究了动力学研究和控制实验以及密度泛函理论 （DFT） 研究以阐明反应机理。