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Paper | Regular issue | Vol 98, No. 10, 2019, pp.1355-1374
Published online, 29th October, 2019
DOI: 10.3987/COM-19-14132
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, and Daisuke Naganuma

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan

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.