School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.
School of Chemistry and Environment, Yunnan Minzu University, Yuehua Street, Kunming 650500, China.
J Org Chem. 2022 Nov 4;87(21):14374-14383. doi: 10.1021/acs.joc.2c01804. Epub 2022 Oct 4.
A convenient and mild protocol for the gold-catalyzed intermolecular coupling of -alkynylphenols with haloalkynes to give vinyl benzofurans is reported. In this work, the gold catalyst SIPrAuCl and the co-catalyst NaBARF would corporately promote the intramolecular cyclization of the -alkynylphenol to benzofuran, and then a selective hydroarylation of benzofuran to haloalkyne was catalyzed by the same catalysts. Computational studies suggest that the hydroarylation process takes place via a concerted nucleophilic attack pathway of the benzofuran to the C2 carbon of the activated haloalkyne, and reveal the original driving force of this hydroarylation process.
本文报道了一种方便、温和的金催化 - 炔基苯酚与卤代炔烃分子间偶联反应制备乙烯基苯并呋喃的方法。在这项工作中，金催化剂 SIPrAuCl 和助催化剂 NaBARF 共同促进 - 炔基苯酚的分子内环化生成苯并呋喃，然后相同的催化剂催化苯并呋喃对卤代炔烃的选择性氢芳基化。计算研究表明，氢芳基化过程是通过苯并呋喃对活化卤代炔烃的 C2 碳的协同亲核进攻途径进行的，并揭示了该氢芳基化过程的原始驱动力。
