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Dual C(sp3)−H Bond Functionalization of N‐Heterocycles through Sequential Visible‐Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions |
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| Authors: | Dr Guo‐Qiang Xu Ji‐Tao Xu Zhi‐Tao Feng Hui Liang Prof?Dr Zhu‐Yin Wang Prof?Dr Yong Qin Prof?Dr Peng‐Fei Xu |
| Institution: | 1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. China;2. Institute of Nanoscience and Nanotechnology, School of Physical Science and Technology, Lanzhou University, Lanzhou, P. R. China |
| Abstract: | Herein we describe a mild method for the dual C(sp3)?H bond functionalization of saturated nitrogen‐containing heterocycles through a sequential visible‐light photocatalyzed dehydrogenation/2+2] cycloaddition procedure. As a complementary approach to the well‐established use of iminium ion and α‐amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3)?H bonds. |
| Keywords: | C− H functionalization [2+2] cycloaddition dehydrogenation synthetic methods visible-light photocatalysis |