Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[b]phosphole oxide via PO-directed lithiation

Ayana Wakatsuki; Mariko Yukimoto; Mao Minoura; Kaori Fujii; Yoshifumi Kimura; Yoshihiro Matano

doi:10.1039/C8DT01503A

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Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[b]phosphole oxide via PO-directed lithiation†

Ayana Wakatsuki,^a Mariko Yukimoto,‡^b Mao Minoura,^b Kaori Fujii,

^c Yoshifumi Kimura

^c and Yoshihiro Matano

*^d

Author affiliations

* Corresponding authors

^a Department of Fundamental Sciences, Graduate School of Science and Technology, Niigata University, Nishi-ku, Niigata 950-2181, Japan

^b Department of Chemistry, College of Science, Rikkyo University, Toshima-ku, Tokyo 171-8501, Japan

^c Department of Applied Chemistry, Graduate School of Science and Engineering, Doshisha University, Kyotanabe 610-0321, Japan

^d Department of Chemistry, Faculty of Science, Niigata University, Nishi-ku, Niigata 950-2181, Japan
E-mail: matano@chem.sc.niigata-u.ac.jp

Abstract

Various 7-substituted benzo[b]phosphole derivatives were prepared by P [double bond, length as m-dash] O-directed lithiation of 1,2,3-triphenylbenzo[b]phosphole P-oxide and subsequent iodination and cross-coupling reactions. The electron-donating groups introduced at the 7-position produced dramatic solvatofluorochromism owing to the strong charge-transfer character of the excited state of the entire π-system.

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DOI: https://doi.org/10.1039/C8DT01503A
Article type: Communication
Submitted: 17 Apr 2018
Accepted: 01 May 2018
First published: 02 May 2018

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Dalton Trans., 2018,47, 7123-7127

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Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[b]phosphole oxide via PO-directed lithiation

A. Wakatsuki, M. Yukimoto, M. Minoura, K. Fujii, Y. Kimura and Y. Matano, Dalton Trans., 2018, 47, 7123 DOI: 10.1039/C8DT01503A

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Dalton Transactions

Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[b]phosphole oxide via PO-directed lithiation†

Abstract

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Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[b]phosphole oxide via PO-directed lithiation

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