Cu(II)催化的α-羰基-γ-炔基亚砜酰亚砜消除对(Z)- 1h -异色胺的环性磺化反应

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC
Peng Zhou*, Hao-Ze Wu, Qiuyun Li, Wen-Juan Hao, Man-Su Tu* and Bo Jiang*, 
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引用次数: 0

摘要

h -同色胺支架在天然产物和重要的生物活性分子中普遍存在。虽然这些分子合成的几种方法已经开发出来,但关于高效构建拟同色胺的报道仍然相当有限。本文报道了一种新的Cu(II)催化的α-羰基-γ-炔基亚砜鎓化物与磺胺的环化和磺化级联反应,可以直接消除C-C σ-键,以51-97%的产率得到消除的(Z)- 1h -异色胺。在反应过程中,亚砜鎓化物单元作为无迹的消除基是成功消除磺化反应的关键,它可以实现Cu(II)催化的N-H插入和随后醋酸介导的C-C σ键消除。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Cu(II)-Catalyzed Annulative Sulfonylimination of α-Carbonyl-γ-alkynyl Sulfoxonium Ylides through Sulfoxonium Ylide Elimination for Access to (Z)-1H-Isochromenes

Cu(II)-Catalyzed Annulative Sulfonylimination of α-Carbonyl-γ-alkynyl Sulfoxonium Ylides through Sulfoxonium Ylide Elimination for Access to (Z)-1H-Isochromenes

1H-Isochromene scaffolds are ubiquitous in natural products and significant bioactive molecules. Although several methods for these molecular syntheses have been developed, reports on the efficient construction of iminated isochromenes are still rather limited. Herein, we report a new Cu(II)-catalyzed annulation and sulfonylimination cascade of α-carbonyl-γ-alkynyl sulfoxonium ylides with sulfamides, enabling direct C–C σ-bond elimination to furnish iminated (Z)-1H-isochromenes in 51–97% yields. During the reaction process, the sulfoxonium ylide unit as a traceless eliminative group is the key to successful sulfonylimination, which enables Cu(II)-catalyzed N–H insertion and subsequent acetic acid-mediated C–C σ-bond elimination.

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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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