TY - JOUR
T1 - 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
AU - Toyota, Kozo
AU - Mutoh, Hirotaka
AU - Kishi, Hiroki
AU - Mikami, Shinichi
AU - Tanaka, Hiroki
AU - Yoshida, Shuhei
AU - Naganuma, Daisuke
N1 - Funding Information:
The authors thank Prof. Takeaki Iwamoto, Tohoku University, for discussion at the early stage of this research. This work was supported in part by Grants-in-Aid for Scientific Research (No. 23655026) from the Ministry of Education, Culture, Supports, Science and Technology, Japanese Government.
Publisher Copyright:
© 2019 The Japan Institute of Heterocyclic Chemistry
PY - 2019
Y1 - 2019
N2 - 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.
AB - 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.
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U2 - 10.3987/COM-19-14132
DO - 10.3987/COM-19-14132
M3 - Article
AN - SCOPUS:85076341809
SN - 0385-5414
VL - 98
SP - 1355
EP - 1374
JO - Heterocycles
JF - Heterocycles
IS - 10
ER -