Ruthenium‐Catalyzed C−C Bond Cleavage of 2H‐Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons |
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Authors: | Tengfei Li Dr Fen Xu Dr Xincheng Li Dr Chunxiang Wang Prof?Dr Boshun Wan |
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Institution: | 1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China;2. Department of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou, China |
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Abstract: | 2H‐azirines can serve as three‐atom synthons by C?C bond cleavage, however, it involves a high energy barrier under thermal conditions (>50.0 kcal mol?1). Reported is a ruthenium‐catalyzed 3+2+2] cycloaddition reaction of 2H‐azirines with diynes, thus leading to the formation of fused azepine skeletons. This approach features an unprecedented metal‐catalyzed C?C bond cleavage of 2H‐azirines at room temperature, and the challenging construction of aza‐seven‐membered rings from diynes. The results of this study provide a new reaction pattern for constructing nitrogen‐containing seven‐membered rings and may find applications in the synthesis of other complex heterocycles. |
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Keywords: | alkynes C− C activation cycloaddition heterocycles ruthenium |
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