Ruthenium-Catalyzed C-C Bond Cleavage of 2H-Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons

Angewandte Chemie
Tengfei LiBoshun Wan

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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Citations

May 19, 2017·Chemical Communications : Chem Comm·Subin ChoiCheol-Min Park
Apr 18, 2018·Organic & Biomolecular Chemistry·Nikolai V RostovskiiMikhail S Novikov
Aug 16, 2017·Chemical Communications : Chem Comm·Hongyu WangBo Tang
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Sep 6, 2018·Chemistry : a European Journal·Filipe GomesAlois Fürstner
Jul 16, 2019·Organic & Biomolecular Chemistry·Junmin HuangWei Zeng
Sep 18, 2020·Chemical Communications : Chem Comm·Qiupeng PengJian Wang
Jul 27, 2020·Chemistry : a European Journal·Barry M TrostJohnathan E Schultz
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Nov 6, 2018·The Journal of Organic Chemistry·Shoujie ShiZhenhua Ding
Nov 27, 2018·The Journal of Organic Chemistry·Manman WangJunbiao Chang
Dec 13, 2018·Organic Letters·Zongyang LiZhenhua Zhang

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