Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C-H Activation with Silyldimesitylborane

Ryosuke Shishido; Ikuo Sasaki; Tomohiro Seki; Tatsuo Ishiyama; Hajime Ito

doi:10.1002/chem.201903776

Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C-H Activation with Silyldimesitylborane

Chemistry. 2019 Oct 8;25(56):12924-12928. doi: 10.1002/chem.201903776. Epub 2019 Sep 11.

Authors

Ryosuke Shishido¹, Ikuo Sasaki², Tomohiro Seki^{1

3}, Tatsuo Ishiyama¹, Hajime Ito^{1

3}

Affiliations

¹ Division of Applied Chemistry, Graduate School of Engineering Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido, 060-8628, Japan.
² Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara, 252-5258, Japan.
³ Institute for Chemical Reaction Design and Discovery (WPI-ICRD), Hokkaido University, Kita 21, Nishi 10, Kita-ku, Sapporo, 001-0021, Japan.

PMID: 31432548
DOI: 10.1002/chem.201903776

Abstract

Direct dimesitylborylation of benzofuran derivatives by a C-H activation catalyzed by an iridium(I)/N-heterocyclic carbene (NHC) complex in the presence of Ph₂ MeSi-BMes₂ afforded the corresponding dimesitylborylation products in good to high yield with excellent regioselectivity. This method provides a straightforward route to donor-(π-spacer)-acceptor systems with intriguing solvatochromic luminescence properties.

Keywords: C−H borylation; benzofuran; dimesitylboryl group; iridium catalyst; silyldimesitylborane.

Abstract

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