Rh-Catalyzed Dehydrogenative Cyclization Leading to Benzosilolothiophene Derivatives via Si-H/C-H Bond Cleavage

Koichi Mitsudo; Seiichi Tanaka; Ryota Isobuchi; Tomohiro Inada; Hiroki Mandai; Toshinobu Korenaga; Atsushi Wakamiya; Yasujiro Murata; Seiji Suga

doi:10.1021/acs.orglett.7b00878

Rh-Catalyzed Dehydrogenative Cyclization Leading to Benzosilolothiophene Derivatives via Si-H/C-H Bond Cleavage

Koichi Mitsudo, Seiichi Tanaka, Ryota Isobuchi, Tomohiro Inada, Hiroki Mandai, Toshinobu Korenaga, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

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

16 Citations (Scopus)

Abstract

Straightforward syntheses leading to π-extended benzosilolothiophene (BST) derivatives by Rh-catalyzed dehydrogenative cyclization reactions have been developed. Electron-deficient ligands were effective for the reactions, and dppe-F₂₀ gave the best result. This method could be applied to the synthesis of highly π-extended ladder-type BST derivatives, which exhibited fluorescence.

Original language	English
Pages (from-to)	2564-2567
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	10
DOIs	https://doi.org/10.1021/acs.orglett.7b00878
Publication status	Published - May 19 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Rh-Catalyzed Dehydrogenative Cyclization Leading to Benzosilolothiophene Derivatives via Si-H/C-H Bond Cleavage. / Mitsudo, Koichi; Tanaka, Seiichi; Isobuchi, Ryota; Inada, Tomohiro; Mandai, Hiroki; Korenaga, Toshinobu; Wakamiya, Atsushi; Murata, Yasujiro; Suga, Seiji.

In: Organic Letters, Vol. 19, No. 10, 19.05.2017, p. 2564-2567.

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

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abstract = "Straightforward syntheses leading to π-extended benzosilolothiophene (BST) derivatives by Rh-catalyzed dehydrogenative cyclization reactions have been developed. Electron-deficient ligands were effective for the reactions, and dppe-F20 gave the best result. This method could be applied to the synthesis of highly π-extended ladder-type BST derivatives, which exhibited fluorescence.",

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note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research (C) (Nos. 25410042, 16K05695) from JSPS, Japan, by the Collaborative Research Program of Institute for Chemical Research, Kyoto University (Grant No. 2015-47), and by JST, ACT-C, Japan.",

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AU - Inada, Tomohiro

AU - Mandai, Hiroki

AU - Korenaga, Toshinobu

AU - Wakamiya, Atsushi

AU - Murata, Yasujiro

AU - Suga, Seiji

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