Unexpected formation of 4,7-dihalobenzo[b]thiophenes using Ohira-Bestmann reagent and reactivity of the halogen-substituted benzo[b]thiophenes in Suzuki-Miyaura coupling with phenylboronic acid

Kozo Toyota, Hirotaka Mutoh, Hiroki Kishi, Shinichi Mikami, Hiroki Tanaka, Shuhei Yoshida, Daisuke Naganuma

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Reaction of 2-(1-adamantylsulfanyl)-3,6-dihalobenzaldehydes with Ohira-Bestmann reagent gave 4,7-dihalobenzo[b]thiophenes along with normal alkyne products. Nine types of 4,7-dihalobenzo[b]thiophenes bearing chlorine, bromine, or iodine atoms, were prepared by this method. Regioselectivity in Suzuki-Miyaura cross coupling reactions of the 4,7-dihalobenzo[b]thiophenes with PhB(OH)2 was also studied.

Original languageEnglish
Pages (from-to)1355-1374
Number of pages20
JournalHeterocycles
Volume98
Issue number10
DOIs
Publication statusPublished - 2019

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Unexpected formation of 4,7-dihalobenzo[b]thiophenes using Ohira-Bestmann reagent and reactivity of the halogen-substituted benzo[b]thiophenes in Suzuki-Miyaura coupling with phenylboronic acid'. Together they form a unique fingerprint.

Cite this