利用金（I）催化的氧化/频哪醇重排/-迈克尔串联反应高效一锅法合成2,4,5-三取代3(2)-呋喃酮
Highly Efficient One-Pot Synthesis of 2,4,5-Trisubstituted 3(2)-Furanones Utilizing a Au(I)-Catalyzed Oxidation/Pinacol Rearrangement/-Michael Cascade.
作者信息
Wu Yanbin, Zang Shuang, Ren Hang, Wang Lingyao, Kong Lichun, Zheng Jianfeng, Li Jun
机构信息
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang 321004, People's Republic of China.
School of Chemistry, Southwest Jiaotong University, Chengdu, Sichuan 610031, People's Republic of China.
出版信息
Org Lett. 2024 Sep 13;26(36):7656-7660. doi: 10.1021/acs.orglett.4c02760. Epub 2024 Sep 3.
A highly efficient Au(I)-catalyzed cascade reaction between bispropargylic alcohols and pyridine--oxides has been realized. The reaction process involved a gold(I)-catalyzed sequential oxidation/Pinacol rearrangement/oxacyclization. Moreover, 1,2-aryl, 1,2-alkyl, or 1,2-vinyl migration was favored over 1,2-alkynyl in the crucial gold(I)-catalyzed Pinacol rearrangement step. A range of 2,4,5-trisubstituted 3(2)-furanones were synthesized in high yields (up to 88%) with excellent regioselectivities (up to >19:1) under mild reaction conditions.
已实现了双炔丙醇与吡啶 - 氧化物之间高效的金（I）催化串联反应。该反应过程涉及金（I）催化的顺序氧化/频哪醇重排/氧环化。此外，在关键的金（I）催化频哪醇重排步骤中，1,2 - 芳基、1,2 - 烷基或1,2 - 乙烯基迁移比1,2 - 炔基迁移更有利。在温和的反应条件下，以高产率（高达88%）和优异的区域选择性（高达>19:1）合成了一系列2,4,5 - 三取代的3(2)-呋喃酮。
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