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Title: One-Pot Synthesis of a bis-Pocket Corrole through a 14-fold Bromination Reaction

Abstract

For a one-pot protocol, effecting 14-fold bromination with elemental bromine, has afforded copper β-octabromo-meso-tris(2,6-dibromo-3,5-dimethoxyphenyl)corrole, a new bis-pocket metallocorrole. The Cu complex underwent smooth demetalation under reductive conditions, affording the free corrole ligand, which in turn could be readily complexed to MnIII and AuIII. Finally, a single-crystal X-ray structure was obtained for the MnIII complex.

Authors:
 [1];  [1];  [2]; ORCiD logo [1]
  1. Arctic Univ. of Norway, Tromso (Norway). Dept. of Chemistry
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Advanced Light Source
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1413720
Grant/Contract Number:  
AC02-05CH11231
Resource Type:
Accepted Manuscript
Journal Name:
ChemistryOpen
Additional Journal Information:
Journal Volume: 6; Journal Issue: 2; Journal ID: ISSN 2191-1363
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; bis-pocket corrole; bromination; complex synthesis; copper; x-ray diffraction

Citation Formats

Norheim, Hans-Kristian, Schneider, Christian, Gagnon, Kevin J., and Ghosh, Abhik. One-Pot Synthesis of a bis-Pocket Corrole through a 14-fold Bromination Reaction. United States: N. p., 2017. Web. doi:10.1002/open.201600168.
Norheim, Hans-Kristian, Schneider, Christian, Gagnon, Kevin J., & Ghosh, Abhik. One-Pot Synthesis of a bis-Pocket Corrole through a 14-fold Bromination Reaction. United States. doi:10.1002/open.201600168.
Norheim, Hans-Kristian, Schneider, Christian, Gagnon, Kevin J., and Ghosh, Abhik. Tue . "One-Pot Synthesis of a bis-Pocket Corrole through a 14-fold Bromination Reaction". United States. doi:10.1002/open.201600168. https://www.osti.gov/servlets/purl/1413720.
@article{osti_1413720,
title = {One-Pot Synthesis of a bis-Pocket Corrole through a 14-fold Bromination Reaction},
author = {Norheim, Hans-Kristian and Schneider, Christian and Gagnon, Kevin J. and Ghosh, Abhik},
abstractNote = {For a one-pot protocol, effecting 14-fold bromination with elemental bromine, has afforded copper β-octabromo-meso-tris(2,6-dibromo-3,5-dimethoxyphenyl)corrole, a new bis-pocket metallocorrole. The Cu complex underwent smooth demetalation under reductive conditions, affording the free corrole ligand, which in turn could be readily complexed to MnIII and AuIII. Finally, a single-crystal X-ray structure was obtained for the MnIII complex.},
doi = {10.1002/open.201600168},
journal = {ChemistryOpen},
number = 2,
volume = 6,
place = {United States},
year = {2017},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 1 work
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Figures / Tables:

Figure 1. Figure 1.: Synthesis of 1-Br14.

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Works referenced in this record:

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    Works referencing / citing this record:

    Revisiting the Electronic Ground State of Copper Corroles
    journal, January 2007

    • Bröring, Martin; Brégier, Frédérique; Cónsul Tejero, Esther
    • Angewandte Chemie International Edition, Vol. 46, Issue 3
    • DOI: 10.1002/anie.200603676

    Electrochemistry of Corroles in Nonaqueous Media
    journal, November 2016


    Gold(I) and Gold(III) Corroles
    journal, October 2011

    • Rabinovich, Elena; Goldberg, Israel; Gross, Zeev
    • Chemistry - A European Journal, Vol. 17, Issue 44
    • DOI: 10.1002/chem.201102348

    Copper Corroles Are Inherently Saddled
    journal, August 2009

    • Alemayehu, Abraham B.; Gonzalez, Emmanuel; Hansen, Lars Kristian
    • Inorganic Chemistry, Vol. 48, Issue 16
    • DOI: 10.1021/ic900744v

    Metal-Ligand Misfits: Facile Access to Rhenium-Oxo Corroles by Oxidative Metalation
    journal, December 2015

    • Einrem, Rune F.; Gagnon, Kevin J.; Alemayehu, Abraham B.
    • Chemistry - A European Journal, Vol. 22, Issue 2
    • DOI: 10.1002/chem.201504307

    Reductive demetalation of manganese corroles: The substituent effect
    journal, August 2008


    Synthesis and Structure of [ m eso -Triarylcorrolato]silver(III)
    journal, March 2003

    • Brückner, Christian; Barta, Cheri A.; Briñas, Raymond P.
    • Inorganic Chemistry, Vol. 42, Issue 5
    • DOI: 10.1021/ic0261171

    Efficient Synthesis of meso-Substituted Corroles in a H 2 O−MeOH Mixture
    journal, May 2006

    • Koszarna, Beata; Gryko, Daniel T.
    • The Journal of Organic Chemistry, Vol. 71, Issue 10
    • DOI: 10.1021/jo060007k

    Zum elektronischen Grundzustand des Kupfercorrols
    journal, January 2007

    • Bröring, Martin; Brégier, Frédérique; Cónsul Tejero, Esther
    • Angewandte Chemie, Vol. 119, Issue 3
    • DOI: 10.1002/ange.200603676

    Nonplanar, Noninnocent, and Chiral: A Strongly Saddled Metallocorrole
    journal, September 2010

    • Alemayehu, Abraham B.; Hansen, Lars Kristian; Ghosh, Abhik
    • Inorganic Chemistry, Vol. 49, Issue 17
    • DOI: 10.1021/ic1008736

    Four-Electron Oxygen Reduction by Brominated Cobalt Corrole
    journal, December 2011

    • Schechter, Alex; Stanevsky, Maria; Mahammed, Atif
    • Inorganic Chemistry, Vol. 51, Issue 1
    • DOI: 10.1021/ic202139f

    The Structural Chemistry of Metallocorroles: Combined X-ray Crystallography and Quantum Chemistry Studies Afford Unique Insights
    journal, March 2012

    • Thomas, Kolle E.; Alemayehu, Abraham B.; Conradie, Jeanet
    • Accounts of Chemical Research, Vol. 45, Issue 8
    • DOI: 10.1021/ar200292d

    Metallocorroles as Non-Precious Metal Electrocatalysts for Highly Efficient Oxygen Reduction in Alkaline Media
    journal, August 2016


    Undecaphenylcorroles
    journal, September 2012

    • Berg, Steffen; Thomas, Kolle E.; Beavers, Christine M.
    • Inorganic Chemistry, Vol. 51, Issue 18
    • DOI: 10.1021/ic301388e

    Improved synthesis of sterically encumbered multibrominated corroles
    journal, October 2014


    A Metallocorrole with Orthogonal Pyrrole Rings
    journal, March 2011

    • Thomas, Kolle E.; Conradie, Jeanet; Hansen, Lars K.
    • European Journal of Inorganic Chemistry, Vol. 2011, Issue 12
    • DOI: 10.1002/ejic.201100170

    Ligand Noninnocence in Coinage Metal Corroles: A Silver Knife-Edge
    journal, September 2015

    • Thomas, Kolle E.; Vazquez-Lima, Hugo; Fang, Yuanyuan
    • Chemistry - A European Journal, Vol. 21, Issue 47
    • DOI: 10.1002/chem.201502150

    A Bulky Bis-Pocket Manganese(V)−Oxo Corrole Complex: Observation of Oxygen Atom Transfer between Triply Bonded Mn V ≡O and Alkene
    journal, September 2009

    • Liu, Hai-Yang; Yam, Fei; Xie, Yu-Tao
    • Journal of the American Chemical Society, Vol. 131, Issue 36
    • DOI: 10.1021/ja905153r

    Improved syntheses of β-octabromo-meso-triarylcorrole derivatives
    journal, December 2015


    Synthesis and Molecular Structure of Gold Triarylcorroles
    journal, December 2011

    • Thomas, Kolle E.; Alemayehu, Abraham B.; Conradie, Jeanet
    • Inorganic Chemistry, Vol. 50, Issue 24
    • DOI: 10.1021/ic202023r

    Recent developments in manganese corrole chemistry
    journal, April 2013

    • Liu, Hai-Yang; Mahmood, Mian HR; Qiu, Sheng-Xiang (Samuel)
    • Coordination Chemistry Reviews, Vol. 257, Issue 7-8
    • DOI: 10.1016/j.ccr.2012.12.017

    Copper β-Octakis(trifluoromethyl)corroles: New Paradigms for Ligand Substituent Effects in Transition Metal Complexes
    journal, November 2008

    • Thomas, Kolle Ekaney; Wasbotten, Ingar H.; Ghosh, Abhik
    • Inorganic Chemistry, Vol. 47, Issue 22
    • DOI: 10.1021/ic801101k

    Molecular structure of a gold β-octakis(trifluoromethyl)- meso -triarylcorrole: an 85° difference in saddling dihedral relative to copper
    journal, April 2012


    A bis-pocket porphyrin
    journal, June 1983

    • Suslick, Kenneth S.; Fox, Mary M.
    • Journal of the American Chemical Society, Vol. 105, Issue 11
    • DOI: 10.1021/ja00349a023

    Synthesis of sterically hindered xanthene-modified iron corroles with catalase-like activity
    journal, January 2013

    • Zyska, Björn; Schwalbe, Matthias
    • Chemical Communications, Vol. 49, Issue 36
    • DOI: 10.1039/c3cc40625c

      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.