Chan Cheng-Lin, Tsao Yong-Ting, Paculba Aira Shayne, Lin Pei-Shan, Tsai Zong-Nan, Chiu Hung-Hsuan, Kunitake Risa, Chiu Ming-Jia, Yeh Chun-Chi, Chiu Cheng-Chau, Liao Hsuan-Hung
Department of Chemistry, National Sun Yat-sen University, Kaohsiung 804201, Taiwan (R.O.C.).
Department of Chemistry, University of Rochester, New York 14627, United States.
Org Lett. 2025 Sep 5;27(35):9593-9598. doi: 10.1021/acs.orglett.5c02448. Epub 2025 Aug 25.
We disclose an autocatalytic electron donor-acceptor (EDA) strategy by reutilizing redox auxiliary byproducts as in situ acceptors, enabling an external initiator-free activation of pro-aromatic dihydroquinazolinones (DHQZs). Spectroscopic and DFT data support the Lewis acid-enhanced aggregate formation where DHQZ serves as both donor and latent acceptor through its quinazolinone byproduct. Kinetic studies reveal a kinetic profile specifically representing autoinductive autocatalysis. This platform enables Giese-type acylation/alkylation, desulfonylation, and Minisci reactions, forging C-C, C-N, C-S, and C-Se bonds under mild conditions.
我们公开了一种自催化电子供体-受体（EDA）策略，该策略通过将氧化还原辅助副产物重新用作原位受体，实现了无外部引发剂的前芳香族二氢喹唑啉酮（DHQZs）的活化。光谱和密度泛函理论（DFT）数据支持路易斯酸增强的聚集体形成，其中DHQZ通过其喹唑啉酮副产物既作为供体又作为潜在受体。动力学研究揭示了一种具体代表自诱导自催化的动力学曲线。该平台能够实现吉斯（Giese）型酰化/烷基化、脱磺酰化和米氏（Minisci）反应，在温和条件下形成碳-碳、碳-氮、碳-硫和碳-硒键。
