金催化活化炔烃与有机碘化合物的螺环化反应：获得3-芳基化、3-烯基化和3-炔基化的螺[4.5]三烯酮

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-09-22 DOI:10.1039/d5qo01065a

Jianyue Bi, Zhenxing Zhang, Yuanhao He, Huajian Li, Xinming Yan, Fen Zhao, Fang Dai, Baomin Fan

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引用次数: 0

摘要

在此，我们报道了通过配体激活的金氧化还原催化，金催化活性炔与有机碘化物的螺旋环化。该反应在温和的条件下顺利进行，不需要外部氧化剂，可以得到一系列3-芳基化、3-烯基化和3-炔基化的螺[4.5]三烯酮，收率很高。这种转化具有广泛的底物范围、良好的官能团耐受性和与杂芳烃体系的相容性。（P，N）配体medalphos促进金催化工艺为合成3-取代的螺[4.5]三烯酮提供了一种新的策略。此外，包括核磁共振和质谱研究在内的机理研究有力地支持了所提出的反应机理。

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Gold-Catalyzed Spirocyclization of Activated Alkynes with Organoiodides: Access to 3-Arylated, 3-Alkenylated, and 3-Alkynylated Spiro[4.5]trienones

Herein, we report the gold-catalyzed spirocyclization of activated alkynes with organoiodides through ligand-enabled gold redox catalysis. The reaction proceeds smoothly under mild conditions and without the need for an external oxidant, affording a series of 3-arylated, 3-alkenylated, and 3-alkynylated spiro[4.5]trienones in good to excellent yields. This transformation exhibits a broad substrate scope, good functional group tolerance, and compatibility with heteroaromatic systems. The (P,N) ligand MeDalphos-facilitated gold-catalyzed process provides a new strategy for the synthesis of 3-substituted spiro[4.5]trienones. Furthermore, mechanistic investigations, including NMR and mass spectrometric studies, strongly support the proposed reaction mechanism.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.