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English:Observation of Borane–Olefin Proximity Interaction Governing the Structure and Reactivity of Boron‐Containing Macrocycles 
Japanese: 村田 幸優, 馬緤 賢太, 菓子田 惇輝, 庄子 良晃, C. Özen, S. Maeda, 福島 孝典.  
English: Y. Murata, K. Matsunagi, J. Kashida, Y. Shoji, C. Özen, S. Maeda, T. Fukushima.  
Language English 
Journal/Book name
English:Angewandte Chemie International Edition 
Volume, Number, Page Vol. 60    Issue 26    Page 14630-14635
Published date Apr. 15, 2021 
Conference name
Conference site
Official URL https://onlinelibrary.wiley.com/doi/10.1002/anie.202103512
DOI https://doi.org/10.1002/anie.202103512
Abstract While attractive interactions between borane and olefin have been postulated to trigger various boron‐mediated organic transformations, proximity structures of these functional groups, other than the formation of weak van der Waals complexes, have never been directly observed. Here we show that a close intramolecular borane‐olefin interaction operates in macrocyclic systems containing borane and olefinic groups obtained by multi‐step 1,2‐carboboration between a strained alkyne and 9‐borafluorene derivatives. Depending on Lewis acidity of the borane moiety and the size of the macrocycles, the magnitude of interaction changes, resulting in different reaction modes. The whole picture of the multi‐step reactions has been revealed experimentally with theoretical supports. The present finding may not only provide a deeper understanding of the fundamental boron‐mediated interaction but also lead to the development of new organic transformations involving molecular activation by boranes.

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