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

G. Stephenson; Silvia Cauteruccio; Julien Doulcet

doi:10.1055/s-0033-1340667

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

G. Stephenson
, Silvia Cauteruccio
, Julien Doulcet

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

10 Citations (Scopus)

Abstract

The use of CuTC (Liebeskind’s catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer which previously has been under-used in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.

Original language	English
Pages (from-to)	701-707
Number of pages	7
Journal	Synlett
Volume	25
Issue number	05
DOIs	https://doi.org/10.1055/s-0033-1340667
Publication status	Published - 2014

Keywords

benzodithiophene
Liebeskind’s catalyst
bis-hydrazone coupling
alkene metathesis
non-photochemical
synthesis

Access to Document

10.1055/s-0033-1340667

2 Finished

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

10 Citations
1 Article

A non-photochemical route to synthesize simple benzo[1,2-b:4,3-b′]dithiophenes: FeCl3-mediated cyclization of dithienyl ethenes
Cauteruccio, S., Dova, D., Graiff, C., Carrara, C., Doulcet, J., Stephenson, G. R. & Licandro, E., 1 Jan 2014, In: New Journal of Chemistry. 38, 6, p. 2241-2244 4 p.
Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Cite this

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

abstract = "The use of CuTC (Liebeskind{\textquoteright}s catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer which previously has been under-used in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.",

keywords = "benzodithiophene, Liebeskind{\textquoteright}s catalyst, bis-hydrazone coupling, alkene metathesis, non-photochemical , synthesis",

author = "G. Stephenson and Silvia Cauteruccio and Julien Doulcet",

year = "2014",

doi = "10.1055/s-0033-1340667",

language = "English",

volume = "25",

pages = "701--707",

journal = "Synlett",

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T1 - Comparison of Ullmann/RCM and Ullmann/bis-hydrazone coupling reactions; New access to benzodithiophenes for dye-sensitized solar cell and thiahelicene applications

AU - Stephenson, G.

AU - Cauteruccio, Silvia

AU - Doulcet, Julien

PY - 2014

Y1 - 2014

N2 - The use of CuTC (Liebeskind’s catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer which previously has been under-used in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.

AB - The use of CuTC (Liebeskind’s catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer which previously has been under-used in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.

KW - benzodithiophene

KW - Liebeskind’s catalyst

KW - bis-hydrazone coupling

KW - alkene metathesis

KW - non-photochemical

KW - synthesis

U2 - 10.1055/s-0033-1340667

DO - 10.1055/s-0033-1340667

M3 - Article

SN - 0936-5214

VL - 25

SP - 701

EP - 707

JO - Synlett

JF - Synlett

IS - 05

ER -

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

Abstract

Keywords

Access to Document

Projects

Highly anisotropic helicene - based NLOphores for 2 photon circular dichroism

INTERREG - IS:CE Chem

Research output

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

Cite this