Regioselective synthesis of tetraalkynylarenes by consecutive dual sonogashira coupling reactions of the bis(triflate) of 4,5-diiodobenzene-1,2- diol

Thomas J. Fisher, Patrick H. Dussault

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross-coupling reactions of the bis(triflate) derivative of 4,5-diiodobenzene-1,2-diol. The initial coupling reactions proceeded with nearly complete selectivity for the reaction at the Ar-I linkages. Subsequent coupling reactions at the Ar-OTf linkages were efficiently conducted. The tetraalkynylarene products are of interest as components of organic molecular materials.

Original languageEnglish (US)
Pages (from-to)2831-2836
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number14
DOIs
StatePublished - May 1 2012

Fingerprint

Derivatives
synthesis
linkages
cross coupling
selectivity
products

Keywords

  • Alkynes
  • Cross-coupling
  • Palladium
  • Regioselectivity

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

@article{62400e7c7ba44a359c600731e3220fb4,
title = "Regioselective synthesis of tetraalkynylarenes by consecutive dual sonogashira coupling reactions of the bis(triflate) of 4,5-diiodobenzene-1,2- diol",
abstract = "The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross-coupling reactions of the bis(triflate) derivative of 4,5-diiodobenzene-1,2-diol. The initial coupling reactions proceeded with nearly complete selectivity for the reaction at the Ar-I linkages. Subsequent coupling reactions at the Ar-OTf linkages were efficiently conducted. The tetraalkynylarene products are of interest as components of organic molecular materials.",
keywords = "Alkynes, Cross-coupling, Palladium, Regioselectivity",
author = "Fisher, {Thomas J.} and Dussault, {Patrick H.}",
year = "2012",
month = "5",
day = "1",
doi = "10.1002/ejoc.201200079",
language = "English (US)",
pages = "2831--2836",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
number = "14",

}

TY - JOUR

T1 - Regioselective synthesis of tetraalkynylarenes by consecutive dual sonogashira coupling reactions of the bis(triflate) of 4,5-diiodobenzene-1,2- diol

AU - Fisher, Thomas J.

AU - Dussault, Patrick H.

PY - 2012/5/1

Y1 - 2012/5/1

N2 - The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross-coupling reactions of the bis(triflate) derivative of 4,5-diiodobenzene-1,2-diol. The initial coupling reactions proceeded with nearly complete selectivity for the reaction at the Ar-I linkages. Subsequent coupling reactions at the Ar-OTf linkages were efficiently conducted. The tetraalkynylarene products are of interest as components of organic molecular materials.

AB - The regioselective synthesis of nonsymmetric tetraalkynylarenes has been readily achieved through consecutive sets of Sonagashira cross-coupling reactions of the bis(triflate) derivative of 4,5-diiodobenzene-1,2-diol. The initial coupling reactions proceeded with nearly complete selectivity for the reaction at the Ar-I linkages. Subsequent coupling reactions at the Ar-OTf linkages were efficiently conducted. The tetraalkynylarene products are of interest as components of organic molecular materials.

KW - Alkynes

KW - Cross-coupling

KW - Palladium

KW - Regioselectivity

UR - http://www.scopus.com/inward/record.url?scp=84860621937&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84860621937&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201200079

DO - 10.1002/ejoc.201200079

M3 - Article

AN - SCOPUS:84860621937

SP - 2831

EP - 2836

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 14

ER -