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| Oxidative C -H alkynylation of 3,6-dihydro-2H-pyrans |
| Ran Zhaoa, Guidong Fengb, Xiaodong Xinc, Honghao Guanc, Jing Huad, Renzhong Wanb, Wei Lia, Lei Liuc |
a Department of Pharmaceutical Analysis, School of Pharmacy, Shandong University of Traditional Chinese Medicine, Ji'nan 250355, China;
b College of Animal Science and Veterinary Medicine, Shandong Agricultural University, Taian 271018, China;
c School of Chemistry and Chemical Engineering, Shandong University, Ji'nan 250100, China;
d State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China |
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| Guide Current synthesis of α-substituted 3,6-dihydro-2H-pyrans dominantly relies on functional group transformation. Herein, a direct and practical oxidative C-H alkynylation and alkenylation of 3,6-dihydro-2H-pyran skeletons with a range of potassium trifluoroborates is developed. The metal-free process is well tolerated with a wide variety of 3,6-dihydro-2H-pyrans, rapidly providing a library of 2,4-disubstituted 3,6-dihydro-2H-pyrans with diverse patterns of α-functionalities for further diversification and bioactive small molecule identification. |
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Abstract Current synthesis of α-substituted 3,6-dihydro-2H-pyrans dominantly relies on functional group transformation. Herein, a direct and practical oxidative C -H alkynylation and alkenylation of 3,6-dihydro-2H-pyran skeletons with a range of potassium trifluoroborates is developed. The metal-free process is well tolerated with a wide variety of 3,6-dihydro-2H-pyrans, rapidly providing a library of 2,4-disubstituted 3,6-dihydro-2H-pyrans with diverse patterns of α-functionalities for further diversification and bioactive small molecule identification.
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Received: 23 February 2019
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| Fund:This work was financial supported by the National Natural Science Foundation of China (No. 21722204), Fok Ying Tung Education Foundation (No. 151035), the Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University) (No. CHEMR2016-B09), and Guangxi Funds for Distinguished expert. |
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Corresponding Authors:
Renzhong Wan, Wei Li, Lei Liu
E-mail: wrzh63@163.com;liwei6911@163.com;leiliu@sdu.edu.cn
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