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0 202606013

DOI: https://doi.org/10.6023/cjoc202606013

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I2-DMSO-Mediated Polarity Reversal of Aryl Methyl Ketones: Access to Heterocycles via Enone Intermediates

  • Jun Ma ,
  • An-Xin Wu
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  • aState Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan, 430079;
    bState Key Laboratory of Natural Product Chemistry, Lanzhou University, Lanzhou, 730000

Received date: 2026-06-13

  Revised date: 2026-07-08

  Online published: 2026-08-24

Supported by

National Natural Science Foundation of China (No. 22571111), the Fundamental Research Funds for the Central Universities (No. CCNU25JC018) and Chengdu Guibao Science & Technology Co., Ltd.

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Abstract

Aryl methyl ketones are cheap, easily accessible starting materials in organic synthesis and key building blocks for natural products and pharmaceuticals. Developing new synthetic methodologies for heterocycles using aryl methyl ketones is therefore of great research value. The combined I2-DMSO reagent system exhibits mild reaction conditions and high reaction efficiency, and has been widely utilized for heterocycle synthesis. Inspired by the polarity reversal of aryl methyl ketones, our group employed the I2-DMSO system to realize the α-iodination and Kornblum oxidation of aryl methyl ketones, which produces highly reactive aryl-substituted 2-oxoacetaldehyde intermediates. These intermediates react with active methylene compounds and 5-aminopyrazole derivatives through enone species to undergo multicomponent cascade cyclization, efficiently affording a broad range of heterocycles such as monocycles, fused rings and spirocycles. This review systematically summarizes our recent advances in I2-DMSO-mediated multicomponent cyclization reactions based on the polarity reversal of aryl methyl ketones for heterocycle construction. The reaction features, substrate scope and underlying mechanisms are discussed, and the future development and application prospects of this research field are also presented.

Key words： aryl methyl ketones; I2-DMSO system; polarity reversal; active methylene compounds; 5-aminopyrazole derivatives; heterocycle synthesis

Cite this article

Jun Ma , An-Xin Wu . I2-DMSO-Mediated Polarity Reversal of Aryl Methyl Ketones: Access to Heterocycles via Enone Intermediates[J]. Chinese Journal of Organic Chemistry, 0 : 202606013 . DOI: 10.6023/cjoc202606013

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