Synthesis and Properties of Dithieno-Fused 1,4-Azaborine Derivatives

Koichi Mitsudo; Keisuke Shigemori; Hiroki Mandai; Atsushi Wakamiya; Seiji Suga

doi:10.1021/acs.orglett.8b03316

Synthesis and Properties of Dithieno-Fused 1,4-Azaborine Derivatives

Org Lett. 2018 Nov 16;20(22):7336-7340. doi: 10.1021/acs.orglett.8b03316. Epub 2018 Oct 29.

Authors

Koichi Mitsudo¹, Keisuke Shigemori¹, Hiroki Mandai¹, Atsushi Wakamiya², Seiji Suga¹

Affiliations

¹ Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushima-naka , Kita-ku , Okayama 700-8530 , Japan.
² Institute for Chemical Research , Kyoto University , Uji , Kyoto 611-0011 , Japan.

PMID: 30372077
DOI: 10.1021/acs.orglett.8b03316

Abstract

The first synthesis of dithieno[3,2- b:2',3'- e][1,4]azaborinine (DTAB) derivatives has been achieved by Buchwald-Hartwig coupling and subsequent Friedel-Crafts-type C-H borylation. A facile method for further π-extension of DTAB was also developed via stannylation and subsequent Kosugi-Migita-Stille cross-coupling reaction. The fundamental properties of DTAB derivatives were also investigated.

Publication types

Research Support, Non-U.S. Gov't