Synthesis of 2,9-dialkylated phenanthro[1,2-b: 8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide

Keita Hyodo, Hikaru Nonobe, Shuhei Nishinaga, Yasushi Nishihara

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Phenanthro[1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents.

Original languageEnglish
Pages (from-to)4002-4005
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number29
DOIs
Publication statusPublished - Jul 16 2014

Fingerprint

Lewis Acids
Epoxy Compounds
Cross Reactions
Zinc Compounds
Derivatives
1-phenyl-3,3-dimethyltriazene

Keywords

  • Boron
  • Negishi coupling
  • Phenacenes
  • Suzuki-Miyaura coupling
  • Zinc

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of 2,9-dialkylated phenanthro[1,2-b : 8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide. / Hyodo, Keita; Nonobe, Hikaru; Nishinaga, Shuhei; Nishihara, Yasushi.

In: Tetrahedron Letters, Vol. 55, No. 29, 16.07.2014, p. 4002-4005.

Research output: Contribution to journalArticle

@article{e13ab766192946d2bc72696e9a31343c,
title = "Synthesis of 2,9-dialkylated phenanthro[1,2-b: 8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide",
abstract = "Phenanthro[1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents.",
keywords = "Boron, Negishi coupling, Phenacenes, Suzuki-Miyaura coupling, Zinc",
author = "Keita Hyodo and Hikaru Nonobe and Shuhei Nishinaga and Yasushi Nishihara",
year = "2014",
month = "7",
day = "16",
doi = "10.1016/j.tetlet.2014.05.035",
language = "English",
volume = "55",
pages = "4002--4005",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "29",

}

TY - JOUR

T1 - Synthesis of 2,9-dialkylated phenanthro[1,2-b

T2 - 8,7-b′]dithiophenes via cross-coupling reactions and sequential Lewis acid-catalyzed regioselective cycloaromatization of epoxide

AU - Hyodo, Keita

AU - Nonobe, Hikaru

AU - Nishinaga, Shuhei

AU - Nishihara, Yasushi

PY - 2014/7/16

Y1 - 2014/7/16

N2 - Phenanthro[1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents.

AB - Phenanthro[1,2-b:8,7-b′]dithiophene (PDT) was prepared via Suzuki-Miyaura or Negishi cross-coupling of a 2-thienylboron or -zinc compound with 1,4-dibromobenzene, followed by Lewis acid-catalyzed regioselective cycloaromatization of the epoxide. A series of 2,9-dialkylated phenanthro[1,2-b:8,7-b′]dithiophene (PDT) derivatives could also be synthesized in good yields by Suzuki-Miyaura coupling of the brominated PDT with alkylboranes by introducing linear alkyl substituents.

KW - Boron

KW - Negishi coupling

KW - Phenacenes

KW - Suzuki-Miyaura coupling

KW - Zinc

UR - http://www.scopus.com/inward/record.url?scp=84903275596&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84903275596&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.05.035

DO - 10.1016/j.tetlet.2014.05.035

M3 - Article

AN - SCOPUS:84903275596

VL - 55

SP - 4002

EP - 4005

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 29

ER -