Rhodium-Catalyzed Cascade Carbene Coupling Reactions of α,α-Difluoro-N-Tosylhydrazones, Arylboronates and Alcohols for the Synthesis of Alkyl Enol Ethers

IF 2.7 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-03-06 DOI:10.1002/ejoc.202401445
Yueting Zhao, Xu Wang, Ran Li, Bingxue Wang, Kefu Gao, Prof. Dr. Pifeng Wei, Prof. Dr. Fangdong Hu
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Abstract

Transition metal-catalyzed cascade carbene coupling reactions are highly valued strategies for the assembly of complex molecules. Among various carbene precursors, α,α-difluoro-N-tosylhydrazones have emerged as promising candidates in such reactions. In this study, we report a rhodium-catalyzed three-component carbene coupling reaction involving α,α-difluoro-N-tosylhydrazones, arylboronates and alcohols. This approach provides a complementary method for the efficient synthesis of alkyl enol ethers, showcasing a broad substrate scope and favorable yields. Additionally, the subsequent transformations of the resulting products demonstrate the synthetic utility and versatility of this protocol.

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铑催化α,α-二氟- n -甲苯腙,芳硼酸酯和醇的级联羰基偶联反应合成烷基烯醇醚
过渡金属催化的级联羰基偶联反应是合成复杂分子的重要手段。在各种碳前体中,α,α-二氟- n -甲苯腙已成为这类反应的有希望的候选者。在这项研究中,我们报道了一个铑催化的三组分碳偶联反应,涉及α,α-二氟- n -甲苯腙,芳基硼酸盐和醇。该方法为烷基烯醇醚的高效合成提供了一种补充方法,显示出广泛的底物范围和良好的产率。此外,结果产品的后续转换演示了该协议的综合实用性和多功能性。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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