A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes

Silvia Cauteruccio; Davide Dova; Claudia Graiff; Claudio Carrara; Julien Doulcet; G. Richard Stephenson; Emanuela Licandro

doi:10.1039/c3nj01567j

A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes

Silvia Cauteruccio, Davide Dova, Claudia Graiff, Claudio Carrara, Julien Doulcet, G. Richard Stephenson, Emanuela Licandro

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

The FeCl3-mediated cyclization of a,a0-disubstituted Z-alkenes 1 is reported as a general and non-photochemical route to synthesize benzo[1,2-b:4,3-b0]dithiophene (BDT) derivatives 2, achievable in good yields starting from cheap and easily available materials. The influence of the temperature and the nature of the substituents on the scope and limitations of this methodology is also reported.

Original language	English
Pages (from-to)	2241-2244
Number of pages	4
Journal	New Journal of Chemistry
Volume	38
Issue number	6
DOIs	https://doi.org/10.1039/c3nj01567j
Publication status	Published - 1 Jan 2014

Keywords

BDT
benzo[1,2-b:4,3-b0]dithiophene
iron(III) chloride
cyclisation
synthesis

Access to Document

10.1039/c3nj01567j

2 Finished

Highly anisotropic helicene - based NLOphores for 2 photon circular dichroism
Stephenson, G. R.
Engineering and Physical Sciences Research Council
1/10/09 → 30/09/13
Project: Research
INTERREG - IS:CE Chem
Stephenson, G. R., Bew, S., Bulman Page, P., Cammidge, A., Goss, R. & Richards, C.
European Regional Development Fund
1/06/08 → 31/05/14
Project: Research

7 Citations (Scopus)
1 Article

Comparison of Ullmann/RCM and Ullmann/bis-hydrazone coupling reactions; New access to benzodithiophenes for dye-sensitized solar cell and thiahelicene applications
Stephenson, G., Cauteruccio, S. & Doulcet, J., 2014, In: Synlett. 25, 05, p. 701-707 7 p.
Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Cite this

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title = "A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes",

abstract = "The FeCl3-mediated cyclization of a,a0-disubstituted Z-alkenes 1 is reported as a general and non-photochemical route to synthesize benzo[1,2-b:4,3-b0]dithiophene (BDT) derivatives 2, achievable in good yields starting from cheap and easily available materials. The influence of the temperature and the nature of the substituents on the scope and limitations of this methodology is also reported.",

keywords = "BDT, benzo[1,2-b:4,3-b0]dithiophene, iron(III) chloride, cyclisation, synthesis",

author = "Silvia Cauteruccio and Davide Dova and Claudia Graiff and Claudio Carrara and Julien Doulcet and Stephenson, {G. Richard} and Emanuela Licandro",

year = "2014",

month = jan,

day = "1",

doi = "10.1039/c3nj01567j",

language = "English",

volume = "38",

pages = "2241--2244",

journal = "New Journal of Chemistry",

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A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes. / Cauteruccio, Silvia; Dova, Davide; Graiff, Claudia; Carrara, Claudio; Doulcet, Julien; Stephenson, G. Richard; Licandro, Emanuela.

In: New Journal of Chemistry, Vol. 38, No. 6, 01.01.2014, p. 2241-2244.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes

AU - Cauteruccio, Silvia

AU - Dova, Davide

AU - Graiff, Claudia

AU - Carrara, Claudio

AU - Doulcet, Julien

AU - Stephenson, G. Richard

AU - Licandro, Emanuela

PY - 2014/1/1

Y1 - 2014/1/1

N2 - The FeCl3-mediated cyclization of a,a0-disubstituted Z-alkenes 1 is reported as a general and non-photochemical route to synthesize benzo[1,2-b:4,3-b0]dithiophene (BDT) derivatives 2, achievable in good yields starting from cheap and easily available materials. The influence of the temperature and the nature of the substituents on the scope and limitations of this methodology is also reported.

AB - The FeCl3-mediated cyclization of a,a0-disubstituted Z-alkenes 1 is reported as a general and non-photochemical route to synthesize benzo[1,2-b:4,3-b0]dithiophene (BDT) derivatives 2, achievable in good yields starting from cheap and easily available materials. The influence of the temperature and the nature of the substituents on the scope and limitations of this methodology is also reported.

KW - BDT

KW - benzo[1,2-b:4,3-b0]dithiophene

KW - iron(III) chloride

KW - cyclisation

KW - synthesis

U2 - 10.1039/c3nj01567j

DO - 10.1039/c3nj01567j

M3 - Article

VL - 38

SP - 2241

EP - 2244

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 6

ER -

A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes

Abstract

Keywords

Access to Document

Projects

Highly anisotropic helicene - based NLOphores for 2 photon circular dichroism

INTERREG - IS:CE Chem

Research output

Comparison of Ullmann/RCM and Ullmann/bis-hydrazone coupling reactions; New access to benzodithiophenes for dye-sensitized solar cell and thiahelicene applications

Cite this