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Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Hong-Xing Zheng, Zu-Feng Xiao, Chuan-Zhi Yao, Qiang-Qiang Li, Xiao-Shan Ning, Yan-Biao Kang* and Yong Tang

*Center of Advanced Nanocatalysis, Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China, Email: ybkangustc.edu.cn

H.-X. Zheng, Z.-F. Xiao, C.-Z. Yao, Q.-Q. Li, X.-S. Ning, Y.-B. Kang, Y. Tang, Org. Lett., 2015, 17, 6102-6105.

DOI: 10.1021/acs.orglett.5b03124 (free Supporting Information)


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Abstract

Phenanthroline and tert-butoxide are powerful radical initiators, that enable a catalyzed transition-metal-free allylic isomerization of allylic alcoholsvia a base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

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Key Words

allylic isomerization


ID: J54-Y2015