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

doi:10.6023/cjoc202606013

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I₂-DMSO组合试剂介导芳基乙酮极性反转：经烯酮中间体构筑杂环

马俊^a, 吴安心^a,b,*

^a华中师范大学化学学院,绿色农药全国重点实验室,智能生物传感技术与健康国际联合研究中心武汉 430079;
^b兰州大学天然产物化学全国重点实验室兰州 730000

收稿日期:2026-06-13 修回日期:2026-07-08
作者简介:马俊，2025年毕业于湖北大学，获理学学士学位。同年进入华中师范大学攻读有机化学专业硕士学位，导师为吴安心教授，主要研究方向为杂环化合物的高效合成。吴安心，华中师范大学教授，博士生导师，国务院政府特殊津贴专家，湖北省有突出贡献中青年专家，武汉市优秀科技工作者。1985 年获兰州大学理学学士学位，1988 年于中国科学院兰州化学物理研究所取得硕士学位。此后他在兰州大学药学院担任助教、讲师共计六年，随后专攻有机合成方向，于兰州大学获得博士学位。1997-2003 年，先后在香港科技大学、美国马里兰大学从事博士后研究。2003年起，受聘为华中师范大学化学学院教授，相继主持国家自然科学基金重点及面上项目十余项。其主要研究方向为杂环化合物的绿色高效合成以及具有重要生物活性天然产物的全合成。
基金资助:
国家自然科学基金(No. 22571111),高校专项基金(No. CCNU25JC018)以及成都硅宝科技股份有限公司资助项目.

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

Jun Ma^a, An-Xin Wu^a,b,*

^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:2026-06-13 Revised:2026-07-08
Contact: ^*E-mail: chwuax@mail.ccnu.edu.cn
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.

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, doi: 10.6023/cjoc202606013.

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I₂-DMSO组合试剂介导芳基乙酮极性反转：经烯酮中间体构筑杂环

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

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I2-DMSO组合试剂介导芳基乙酮极性反转：经烯酮中间体构筑杂环