Synthesis of hexa(furan-2-yl)benzenes and their π-extended derivatives

Koichi Mitsudo; Jyunji Harada; Yo Tanaka; Hiroki Mandai; Chie Nishioka; Hideo Tanaka; Atsushi Wakamiya; Yasujiro Murata; Seiji Suga

doi:10.1021/jo302652r

Synthesis of hexa(furan-2-yl)benzenes and their π-extended derivatives

J Org Chem. 2013 Mar 15;78(6):2763-8. doi: 10.1021/jo302652r. Epub 2013 Mar 6.

Authors

Koichi Mitsudo¹, Jyunji Harada, Yo Tanaka, Hiroki Mandai, Chie Nishioka, Hideo Tanaka, Atsushi Wakamiya, Yasujiro Murata, Seiji Suga

Affiliation

¹ Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan. mitsudo@cc.okayama-u.ac.jp

PMID: 23438033
DOI: 10.1021/jo302652r

Abstract

The first synthesis of hexa(furan-2-yl)benzene derivatives is described. The RhCl3/i-Pr2NEt-catalyzed cyclotrimerization of di(furan-2-yl)acetylenes was an effective method for constructing hexa(furan-2-yl)benzene derivatives in good yields. Their π-extended derivatives were also synthesized by Suzuki-Miyaura coupling between hexakis(5-Bpinfuran-2-yl)benzene (Bpin = (pinacolato)boryl) and several aryl iodides.