@article{99850034014a4732a3223aca9cbb2b6d,
title = "1,4-Dehydrogenation with a Two-Coordinate Cyclic (Alkyl)(amino)silylene",
abstract = "Cyclic (alkyl)(amino)silylene (CAASi) 1 has been found to successfully dehydrogenate 1,4-dihydroaromatic compounds containing various substituents to afford the corresponding aromatic compounds. The observed high substrate generality proves 1 to be a potential 1,4-dehydrogenation reagent for organic compounds. For the reaction with 9,10-dimethyl-9,10-dihydroanthracene, silylene 1 activated not only benzylic C−H bonds but also aromatic C−H bonds to yield a silaacenaphthene derivative, which is an unprecedented reaction of silylenes. The results of the experimental and computational study of the reaction of CAASi 1 with 9,10-dihydroanthracene and 1,4-cyclohexadiene are consistent with the notion that 1,4-dehydrogenation with CAASi 1 proceeds mainly through a stepwise hydrogen-abstraction mechanism.",
keywords = "C−H activation, aromatic compounds, dehydrogenation, main-group elements, reaction mechanisms, silylenes",
author = "Taichi Koike and Tomoyuki Kosai and Takeaki Iwamoto",
note = "Funding Information: This work was supported by MEXT KAKENHI (grant JP24109004 to T.I., Grant-in-Aid for Scientific Research on Innovative Areas “Stimuli-responsive Chemical Species”) and the JSPS KAKENHI (grant JP15K13634 to T.I.). The authors thank Prof. Yujiro Haya-shi (Tohoku University) for helpful advice in the synthesis of the deuterated substrate and Prof. Martin Oestreich (Techni-sche Universit{\"a}t Berlin) for helpful discussions on the reaction mechanism. Funding Information: This work was supported by MEXT KAKENHI (grant JP24109004 to T.I., Grant-in-Aid for Scientific Research on Innovative Areas ?Stimuli-responsive Chemical Species?) and the JSPS KAKENHI (grant JP15K13634 to T.I.). The authors thank Prof. Yujiro Hayashi (Tohoku University) for helpful advice in the synthesis of the deuterated substrate and Prof. Martin Oestreich (Technische Universit?t Berlin) for helpful discussions on the reaction mechanism. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2019",
month = jul,
day = "11",
doi = "10.1002/chem.201901407",
language = "English",
volume = "25",
pages = "9295--9302",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "39",
}