Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

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]
+ Show Author Affiliations
  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 Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
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.
Copy to clipboard
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. https://doi.org/10.1002/open.201600168
Copy to clipboard
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. https://doi.org/10.1002/open.201600168. https://www.osti.gov/servlets/purl/1413720.
Copy to clipboard
@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 = {Tue Feb 14 00:00:00 EST 2017},
month = {Tue Feb 14 00:00:00 EST 2017}
}
Copy to clipboard
Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1002/open.201600168
Copyright Statement
Other availability
Search WorldCat Search WorldCat to find libraries that may hold this journal
Citation Metrics:
Cited by: 3 works
Citation information provided by
Web of Science

Figures / Tables:

Figure 1. Figure 1.: Synthesis of 1-Br14.
All figures and tables (6 total)
Save / Share:
Export Metadata
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.

Works referenced in this record:

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

Reductive demetalation of copper corroles: first simple route to free-base β-octabromocorroles
journal, August 2008

  • Capar, Can; Thomas, Kolle Ekaney; Ghosh, Abhik
  • Journal of Porphyrins and Phthalocyanines, Vol. 12, Issue 08
  • DOI: 10.1142/S1088424608000340

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

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

Gold corroles
journal, February 2011

  • Alemayehu, Abraham B.; Ghosh, Abhik
  • Journal of Porphyrins and Phthalocyanines, Vol. 15, Issue 02
  • DOI: 10.1142/S1088424611003045

Effect of bromination on the electrochemistry, frontier orbitals, and spectroscopy of metallocorroles
journal, November 2011

  • Mahammed, Atif; Tumanskii, Boris; Gross, Zeev
  • Journal of Porphyrins and Phthalocyanines, Vol. 15, Issue 11n12
  • DOI: 10.1142/S1088424611004191

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

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

Improved synthesis of sterically encumbered multibrominated corroles
journal, October 2014

Epoxidation Catalysis by a Manganese Corrole and Isolation of an Oxomanganese(V) Corrole
journal, November 2000

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

β-octabromo- meso -tris(pentafluorophenyl)corrole: reductive demetalation-based synthesis of a heretofore inaccessible, perhalogenated free-base corrole
journal, June 2010

  • Capar, Can; Hansen, Lars-Kristian; Conradie, Jeanet
  • Journal of Porphyrins and Phthalocyanines, Vol. 14, Issue 06
  • DOI: 10.1142/S1088424610002331

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

Highly brominated porphyrins: synthesis, structure and their properties
journal, October 2003

  • Bhyrappa, Puttaiah; Purushothaman, Bhavana; Vittal, Jagadese J.
  • Journal of Porphyrins and Phthalocyanines, Vol. 07, Issue 10
  • DOI: 10.1142/S1088424603000859

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

Oxygen atom transfer reactions from sterically encumbered brominated (oxo)manganese(V) corroles to styrene
journal, December 2015

  • Mahmood, Mian HR; Wang, Hua-Hua; Liu, Hai-Yang
  • Journal of Porphyrins and Phthalocyanines, Vol. 19, Issue 12
  • DOI: 10.1142/S1088424615501059

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

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

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

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

Reductive demetallation of Cu-corroles—a new protective strategy towards functional free-base corroles
journal, January 2009

  • Ngo, Thien Huynh; Van Rossom, Wim; Dehaen, Wim
  • Org. Biomol. Chem., Vol. 7, Issue 3
  • DOI: 10.1039/B819185A

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

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

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

Transition Metal Corrole Coordination Chemistry
book, January 2011

  • Palmer, Joshua H.
  • Molecular Electronic Structures of Transition Metal Complexes I
  • DOI: 10.1007/430_2011_52

Electrochemistry of Corroles in Nonaqueous Media
journal, November 2016

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

Undecaphenylcorroles
journal, September 2012

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

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

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

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

Epoxidation Catalysis by a Manganese Corrole and Isolation of an Oxomanganese(V) Corrole
journal, November 2000

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

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, October 2015

  • Thomas, Kolle E.; Vazquez-Lima, Hugo; Fang, Yuanyuan
  • Chemistry - A European Journal, Vol. 21, Issue 47
  • DOI: 10.1002/chem.201503939

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

  • Thomas, Kolle Ekaney; Wasbotten, Ingar H.; Ghosh, Abhik
  • Inorganic Chemistry, Vol. 48, Issue 3
  • DOI: 10.1021/ic802317e

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

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

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

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

Undecaphenylcorroles
journal, September 2012

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

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

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
    Sort by:
    [ × clear filter / sort ]

    Figures / Tables found in this record:

    Figure 1. (p. 2)figure
    Figure 2. (p. 3)figure
    Figure 3. (p. 3)figure
    Table 1. (p. 3)table
    Figure 4. (p. 4)figure
    Table 2. (p. 4)table
      [ × clear filter / sort ]
      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.

      Similar Records in DOE PAGES and OSTI.GOV collections:

      Other research related to this record: