Literature DB >> 29927588

Gram-Scale Synthesis of a Bench-Stable 5,5″-Unsubstituted Terpyrrole.

James T Brewster1, Hadiqa Zafar1, Matthew McVeigh1, Christopher D Wight1, Gonzalo Anguera1, Axel Steinbrück1, Vincent M Lynch1, Jonathan L Sessler1,2.   

Abstract

The controlled preparation of higher order oligopyrrolic species holds broad utility across the chemical and material sciences. Here, we describe the gram-scale synthesis of a bench-stable 5,5″-unsubstituted terpyrrole in excellent yield via a tandem Suzuki cross-coupling with in situ deprotection. The solution and solid-state stability as well as UV-vis, fluorescence, and single crystal X-ray diffraction structure are also detailed.

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Year:  2018        PMID: 29927588      PMCID: PMC6381930          DOI: 10.1021/acs.joc.8b01333

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  9 in total

1.  One-pot synthesis of substituted 2,2'-bipyrroles. A straightforward route to aryl porphycenes.

Authors:  David Sánchez-García; José I Borrell; Santi Nonell
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

2.  Quaterpyrroles as building blocks for the synthesis of expanded porphyrins.

Authors:  Gonzalo Anguera; Brice Kauffmann; José I Borrell; Salvador Borrós; David Sánchez-García
Journal:  Org Lett       Date:  2015-04-22       Impact factor: 6.005

3.  Pyrrole and oligopyrrole synthesis by 1,3-dipolar cycloaddition of azomethine ylides with sulfonyl dipolarophiles.

Authors:  Rocío Robles-Machín; Ana López-Pérez; María González-Esguevillas; Javier Adrio; Juan Carlos Carretero
Journal:  Chemistry       Date:  2010-08-23       Impact factor: 5.236

4.  Atomistic Engineering of Chemiluminogens: Synthesis, Properties and Polymerization of 2,3-Dihydro-Pyrrolo[3,4-d]Pyridazine-1,4-Dione Scaffolds.

Authors:  Melek Pamuk Algi; Zahide Oztas; Seha Tirkeş; Atilla Cihaner; Fatih Algi
Journal:  J Fluoresc       Date:  2016-11-18       Impact factor: 2.217

Review 5.  2,2'-Bipyrrole-Based Porphyrinoids.

Authors:  Jun-Ichiro Setsune
Journal:  Chem Rev       Date:  2016-11-01       Impact factor: 60.622

6.  Facile syntheses of quater-, penta-, and sexipyrroles.

Authors:  Jonathan L Sessler; Apolonio Aguilar; David Sanchez-Garcia; Daniel Seidel; Thomas Köhler; Forrest Arp; Vincent M Lynch
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

Review 7.  Fluorescent and colorimetric ion probes based on conjugated oligopyrroles.

Authors:  Yubin Ding; Yunyu Tang; Weihong Zhu; Yongshu Xie
Journal:  Chem Soc Rev       Date:  2015-03-07       Impact factor: 54.564

8.  Oligopyrrole synthesis by 1,3-dipolar cycloaddition of azomethine ylides with bissulfonyl ethylenes.

Authors:  Ana López-Pérez; Rocío Robles-Machín; Javier Adrio; Juan Carlos Carretero
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

9.  First-principles study of terpyrrole as a potential hydrogen cyanide sensor: DFT calculations.

Authors:  Ali Shokuhi Rad; Mohammad Reza Zardoost; Ehsan Abedini
Journal:  J Mol Model       Date:  2015-09-29       Impact factor: 1.810

  9 in total

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