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Title: Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination

Abstract

Terminal copper-nitrenoid complexes have inspired interest in their fundamental bonding structures as well as their putative intermediacy in catalytic nitrene-transfer reactions. Here, we report that aryl azides react with a copper(I) dinitrogen complex bearing a sterically encumbered dipyrrin ligand to produce terminal copper nitrene complexes with near-linear, short copper–nitrenoid bonds [1.745(2) to 1.759(2) angstroms]. X-ray absorption spectroscopy and quantum chemistry calculations reveal a predominantly triplet nitrene adduct bound to copper(I), as opposed to copper(II) or copper(III) assignments, indicating the absence of a copper−nitrogen multiple-bond character. Employing electron-deficient aryl azides renders the copper nitrene species competent for alkane amination and alkene aziridination, lending further credence to the intermediacy of this species in proposed nitrene-transfer mechanisms.

Authors:
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Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1561413
Grant/Contract Number:  
AC02-76SF00515; 10048
Resource Type:
Published Article
Journal Name:
Science
Additional Journal Information:
Journal Name: Science Journal Volume: 365 Journal Issue: 6458; Journal ID: ISSN 0036-8075
Publisher:
American Association for the Advancement of Science (AAAS)
Country of Publication:
United States
Language:
English

Citation Formats

Carsch, Kurtis M., DiMucci, Ida M., Iovan, Diana A., Li, Alex, Zheng, Shao-Liang, Titus, Charles J., Lee, Sang Jun, Irwin, Kent D., Nordlund, Dennis, Lancaster, Kyle M., and Betley, Theodore A. Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination. United States: N. p., 2019. Web. doi:10.1126/science.aax4423.
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Carsch, Kurtis M., DiMucci, Ida M., Iovan, Diana A., Li, Alex, Zheng, Shao-Liang, Titus, Charles J., Lee, Sang Jun, Irwin, Kent D., Nordlund, Dennis, Lancaster, Kyle M., & Betley, Theodore A. Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination. United States. https://doi.org/10.1126/science.aax4423
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Carsch, Kurtis M., DiMucci, Ida M., Iovan, Diana A., Li, Alex, Zheng, Shao-Liang, Titus, Charles J., Lee, Sang Jun, Irwin, Kent D., Nordlund, Dennis, Lancaster, Kyle M., and Betley, Theodore A. Thu . "Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination". United States. https://doi.org/10.1126/science.aax4423.
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@article{osti_1561413,
title = {Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination},
author = {Carsch, Kurtis M. and DiMucci, Ida M. and Iovan, Diana A. and Li, Alex and Zheng, Shao-Liang and Titus, Charles J. and Lee, Sang Jun and Irwin, Kent D. and Nordlund, Dennis and Lancaster, Kyle M. and Betley, Theodore A.},
abstractNote = {Terminal copper-nitrenoid complexes have inspired interest in their fundamental bonding structures as well as their putative intermediacy in catalytic nitrene-transfer reactions. Here, we report that aryl azides react with a copper(I) dinitrogen complex bearing a sterically encumbered dipyrrin ligand to produce terminal copper nitrene complexes with near-linear, short copper–nitrenoid bonds [1.745(2) to 1.759(2) angstroms]. X-ray absorption spectroscopy and quantum chemistry calculations reveal a predominantly triplet nitrene adduct bound to copper(I), as opposed to copper(II) or copper(III) assignments, indicating the absence of a copper−nitrogen multiple-bond character. Employing electron-deficient aryl azides renders the copper nitrene species competent for alkane amination and alkene aziridination, lending further credence to the intermediacy of this species in proposed nitrene-transfer mechanisms.},
doi = {10.1126/science.aax4423},
journal = {Science},
number = 6458,
volume = 365,
place = {United States},
year = {Thu Sep 12 00:00:00 EDT 2019},
month = {Thu Sep 12 00:00:00 EDT 2019}
}
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Terminal Nitrido and Imido Complexes of the late Transition Metals
journal, March 2009

Catalytic C−H Bond Amination from High-Spin Iron Imido Complexes
journal, April 2011

  • King, Evan R.; Hennessy, Elisabeth T.; Betley, Theodore A.
  • Journal of the American Chemical Society, Vol. 133, Issue 13
  • DOI: 10.1021/ja110066j

Azides: their preparation and synthetic uses
journal, March 1988

  • Scriven, Eric F. V.; Turnbull, Kenneth
  • Chemical Reviews, Vol. 88, Issue 2
  • DOI: 10.1021/cr00084a001

The (Porphyrin)ruthenium-Catalyzed Aziridination of Olefins Using Aryl Azides as Nitrogen Sources
journal, December 2007

  • Fantauzzi, Simone; Gallo, Emma; Caselli, Alessandro
  • European Journal of Organic Chemistry, Vol. 2007, Issue 36
  • DOI: 10.1002/ejoc.200700678

Scrutinizing metal–ligand covalency and redox non-innocence via nitrogen K-edge X-ray absorption spectroscopy
journal, January 2019

  • Lukens, James T.; DiMucci, Ida M.; Kurogi, Takashi
  • Chemical Science, Vol. 10, Issue 19
  • DOI: 10.1039/C8SC03350A
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