Chai Te-Jung, Chiou Xin-Shun, Lin Nian-Xuan, Kuo Yu-Tsen, Lin Cheng-Kun
Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.
Org Biomol Chem. 2023 Sep 27;21(37):7541-7545. doi: 10.1039/d3ob01318a.
We present a novel approach for generation of acyloxyphosphoniums by premixing iodobenzene dicarboxylates and triphenylphosphine, resulting in efficient thioester synthesis (up to 100% yield). Stable solid iodobenzene dicarboxylates, achieved carboxylate exchange, serve as hypervalent iodine precursors. The resulting acyloxyphosphoniums allow convenient one-pot thioester synthesis under mild conditions. Our method demonstrates facile acyloxyphosphonium production from iodobenzene dicarboxylates and PhP, enabling diverse thioester preparation. ESI-MS analysis confirms acyloxyphosphonium ion formation, pivotal in acylation. This strategy holds potential for combinatorial thioester synthesis and broader nucleophile modification applications.
我们提出了一种通过预混合二羧酸碘苯酯和三苯基膦来生成酰氧基鏻盐的新方法，该方法可高效合成硫酯（产率高达100%）。通过羧酸盐交换获得的稳定固态二羧酸碘苯酯可作为高价碘前体。生成的酰氧基鏻盐能在温和条件下方便地进行一锅法硫酯合成。我们的方法展示了从二羧酸碘苯酯和PhP轻松制备酰氧基鏻盐的过程，可实现多种硫酯的制备。电喷雾电离质谱（ESI-MS）分析证实了酰氧基鏻离子的形成，这在酰化反应中至关重要。该策略在组合硫酯合成以及更广泛的亲核试剂修饰应用方面具有潜力。
