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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Recent advances in radical addition/divergent cyclization of ynones
Liji Gu1, Ruoyang Xu1, Weiwei Huan2
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 321004 Jinhua, China. zhangyan001@zjnu.edu.cn.
Abstract:
Over the past decade, the design of new radical reactions has emerged as an increasingly powerful strategy for constructing complex molecular scaffolds, typically characterized by predictable yet divergent reaction outcomes, a wide range of radical precursors, and various modes of initiation. Notably, radical cascade addition reactions serve as an efficient and practical strategy for constructing cyclic compounds. The scope of intermolecular radical acceptors is usually limited to C-C double or triple bonds. Compared to alkenes, radical addition to alkynes presents greater challenges. The regioselectivity in the radical addition step to internal alkynes can be controlled by adjusting the electronic effects of the substrate. Ynones are classic radical acceptors in organic synthesis, and many types of bio-relevant cyclic compounds could be obtained by cascade radical cyclization reactions. This review summarizes recent research advances in radical addition/cyclization reactions of ynones. We organized the content of this review based on the structures of the products to provide readers with a clearer overview and deeper understanding, hoping that this work will stimulate future research in this field.
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