Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel-Crafts C-H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives

Keisuke Shigemori; Momoka Watanabe; Julie Kong; Koichi Mitsudo; Atsushi Wakamiya; Hiroki Mandai; Seiji Suga

doi:10.1021/acs.orglett.9b00485

Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel-Crafts C-H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives

Org Lett. 2019 Apr 5;21(7):2171-2175. doi: 10.1021/acs.orglett.9b00485. Epub 2019 Mar 7.

Authors

Keisuke Shigemori¹, Momoka Watanabe¹, Julie Kong¹, Koichi Mitsudo¹, Atsushi Wakamiya², Hiroki Mandai¹, 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: 30843697
DOI: 10.1021/acs.orglett.9b00485

Abstract

The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2'-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure.

Publication types

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