HBr/ dmso介导的γ-酮砜氧化脱氢制γ-酮乙烯基砜

IF 2.3 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2026-10-09 DOI:10.1002/ajoc.70562

Zhenlei Zhang, Wei Zhao, Manqi Zhang, Xiaozhen Li, Jun Yu, Jiaojiao Xu, Tianyou Zhang

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引用次数: 0

摘要

γ-酮基砜是有价值的合成中间体，但有效的制备方法仍然有限。在此，我们报道了HBr/ dmso介导的γ-酮砜氧化脱氢成γ-酮基砜。这种无过渡金属的方案无需外部氧化剂，具有广泛的底物范围和良好的官能团耐受性。机制研究支持hbr促进烯化-溴化-脱氢溴化途径。进一步的E/Z光异构化和溴化反应突出了产物的合成实用性。

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HBr/DMSO-Mediated Oxidative Dehydrogenation of γ-Keto Sulfones to γ-Keto Vinyl Sulfones

γ-Keto vinyl sulfones are valuable synthetic intermediates, yet efficient methods for their preparation remain limited. Herein, we report an HBr/DMSO-mediated oxidative dehydrogenation of γ-keto sulfones to γ-keto vinyl sulfones. This transition-metal-free protocol proceeds without external oxidants and features broad substrate scope and good functional-group tolerance. Mechanistic studies support an HBr-promoted enolization–bromination–dehydrobromination pathway. Further E/Z photoisomerization and bromination highlight the synthetic utility of the products.

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.