One-pot condensation of a bicyclo[1.1.1]pentasilane through elimination of iodotrimethylsilane assisted by a lewis base

Yuki Yokouchi; Takeaki Iwamoto

doi:10.1021/acs.organomet.0c00514

One-pot condensation of a bicyclo[1.1.1]pentasilane through elimination of iodotrimethylsilane assisted by a lewis base

Yuki Yokouchi, Takeaki Iwamoto

SCI - Chemistry

Tohoku University

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

Development of efficient bond formation reactions remains important in organic and main-group-element chemistry. Herein, we report the metal-free one-pot condensation reaction of 1-iodo-3-trimethylsilyl-substituted bicyclo[1.1.1]pentasilane (BPS) in the presence of 4-(dimethylamino)pyridine (DMAP) providing oligomers of BPS, persila[n]staffanes (n = 2, 3), which involves the successive Si−Si bond formation reaction accompanied by the concomitant formation of iodotrimethylsilane (TMSI) in the form of a DMAP complex. The computational study suggests that the formation of a pentasila[1.1.1]propellane−DMAP complex resulting from the elimination of TMSI from the BPS is a key intermediate.

Original language	English
Pages (from-to)	3301-3305
Number of pages	5
Journal	Organometallics
Volume	39
Issue number	18
DOIs	https://doi.org/10.1021/acs.organomet.0c00514
Publication status	Published - 2020 Sept 28

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title = "One-pot condensation of a bicyclo[1.1.1]pentasilane through elimination of iodotrimethylsilane assisted by a lewis base",

abstract = "Development of efficient bond formation reactions remains important in organic and main-group-element chemistry. Herein, we report the metal-free one-pot condensation reaction of 1-iodo-3-trimethylsilyl-substituted bicyclo[1.1.1]pentasilane (BPS) in the presence of 4-(dimethylamino)pyridine (DMAP) providing oligomers of BPS, persila[n]staffanes (n = 2, 3), which involves the successive Si−Si bond formation reaction accompanied by the concomitant formation of iodotrimethylsilane (TMSI) in the form of a DMAP complex. The computational study suggests that the formation of a pentasila[1.1.1]propellane−DMAP complex resulting from the elimination of TMSI from the BPS is a key intermediate.",

author = "Yuki Yokouchi and Takeaki Iwamoto",

note = "Funding Information: This work was supported in part by JSPS KAKENHI Grants JP25248010, JP15K13634, and JP17H03015 (T.I.) and a research grant from the Institute for Quantum Chemical Exploration (IQCE) (T.I. and Y.Y.). The authors thank Prof. Shintaro Ishida (Tohoku University) for helpful discussion on the XRD analysis. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = sep,

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doi = "10.1021/acs.organomet.0c00514",

language = "English",

volume = "39",

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T1 - One-pot condensation of a bicyclo[1.1.1]pentasilane through elimination of iodotrimethylsilane assisted by a lewis base

AU - Yokouchi, Yuki

AU - Iwamoto, Takeaki

N1 - Funding Information: This work was supported in part by JSPS KAKENHI Grants JP25248010, JP15K13634, and JP17H03015 (T.I.) and a research grant from the Institute for Quantum Chemical Exploration (IQCE) (T.I. and Y.Y.). The authors thank Prof. Shintaro Ishida (Tohoku University) for helpful discussion on the XRD analysis. Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/9/28

Y1 - 2020/9/28

N2 - Development of efficient bond formation reactions remains important in organic and main-group-element chemistry. Herein, we report the metal-free one-pot condensation reaction of 1-iodo-3-trimethylsilyl-substituted bicyclo[1.1.1]pentasilane (BPS) in the presence of 4-(dimethylamino)pyridine (DMAP) providing oligomers of BPS, persila[n]staffanes (n = 2, 3), which involves the successive Si−Si bond formation reaction accompanied by the concomitant formation of iodotrimethylsilane (TMSI) in the form of a DMAP complex. The computational study suggests that the formation of a pentasila[1.1.1]propellane−DMAP complex resulting from the elimination of TMSI from the BPS is a key intermediate.

AB - Development of efficient bond formation reactions remains important in organic and main-group-element chemistry. Herein, we report the metal-free one-pot condensation reaction of 1-iodo-3-trimethylsilyl-substituted bicyclo[1.1.1]pentasilane (BPS) in the presence of 4-(dimethylamino)pyridine (DMAP) providing oligomers of BPS, persila[n]staffanes (n = 2, 3), which involves the successive Si−Si bond formation reaction accompanied by the concomitant formation of iodotrimethylsilane (TMSI) in the form of a DMAP complex. The computational study suggests that the formation of a pentasila[1.1.1]propellane−DMAP complex resulting from the elimination of TMSI from the BPS is a key intermediate.

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IS - 18

ER -

One-pot condensation of a bicyclo[1.1.1]pentasilane through elimination of iodotrimethylsilane assisted by a lewis base

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