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

Title: Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands

Abstract

The trityl-substituted bisoxazoline (TrHBOX) was prepared as a chiral analogue to a previously reported nickel dipyrrin system capable of ring-closing amination catalysis. Ligand metalation with divalent NiI2(py)4 followed by potassium graphite reduction afforded the monovalent (TrHBOX)Ni(py) (4). Slow addition of 1.4 equiv of a benzene solution of 1-adamantylazide to 4 generated the tetrazido (TrHBOX)Ni(κ2-N4Ad2) (5) and terminal iminyl adduct (TrHBOX)Ni(NAd) (6). Investigation of 6 via single-crystal X-ray crystallography, NMR and EPR spectroscopies, and computations revealed a Ni(II)-iminyl radical formulation, similar to its dipyrrinato congener. Complex 4 exhibits enantioselective intramolecular C–H bond amination to afford N-heterocyclic products from 4-aryl-2-methyl-2-azidopentanes. Catalytic C–H amination occurs under mild conditions (5 mol % catalyst, 60 °C) and provides pyrrolidine products in decent yield (29%–87%) with moderate ee (up to 73%). Substrates with a 3,5-dialkyl substitution on the 4-aryl position maximized the observed enantioselectivity. Kinetic studies to probe the reaction mechanism were conducted using 1H and 19F NMR spectroscopies. A small, intermolecular kinetic isotope effect (1.35 ± 0.03) suggests an H-atom abstraction step with an asymmetric transition state while the reaction rate is measured to be first order in catalyst and zeroth order in substrate concentrations. Enantiospecific deuterium labeling studies show that the enantioselectivity is dictatedmore » by both the H-atom abstraction and radical recombination steps due to the comparable rate between radical rotation and C–N bond formation. Furthermore, the competing elements of the two-step reaction where H-removal from the pro-R configuration is preferred while the preferential radical capture occurs with the Si face of the carboradical likely lead to the diminished ee observed, as corroborated by theoretical calculations. Furthermore, based on these enantio-determining steps, catalytic enantioselective synthesis of 2,5-bis-tertiary pyrrolidines is demonstrated with good yield (50–78%) and moderate ee (up to 79%).« less

Authors:
ORCiD logo [1];  [2]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]
+ Show Author Affiliations
  1. Harvard Univ., Cambridge, MA (United States)
  2. Univ. of North Texas, Denton, TX (United States)
Publication Date:
Research Org.:
Univ. of North Texas, Denton, TX (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1831108
Grant/Contract Number:  
FG02-03ER15387
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 143; Journal Issue: 2; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Pyrrolidines; Catalysts; Azides; Ligands; Organic reactions

Citation Formats

Dong, Yuyang, Lund, Colton J., Porter, Gerard J., Clarke, Ryan M., Zheng, Shao-Liang, Cundari, Thomas R., and Betley, Theodore A. Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands. United States: N. p., 2021. Web. doi:10.1021/jacs.0c09839.
Copy to clipboard
Dong, Yuyang, Lund, Colton J., Porter, Gerard J., Clarke, Ryan M., Zheng, Shao-Liang, Cundari, Thomas R., & Betley, Theodore A. Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands. United States. https://doi.org/10.1021/jacs.0c09839
Copy to clipboard
Dong, Yuyang, Lund, Colton J., Porter, Gerard J., Clarke, Ryan M., Zheng, Shao-Liang, Cundari, Thomas R., and Betley, Theodore A. Mon . "Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands". United States. https://doi.org/10.1021/jacs.0c09839. https://www.osti.gov/servlets/purl/1831108.
Copy to clipboard
@article{osti_1831108,
title = {Enantioselective C–H Amination Catalyzed by Nickel Iminyl Complexes Supported by Anionic Bisoxazoline (BOX) Ligands},
author = {Dong, Yuyang and Lund, Colton J. and Porter, Gerard J. and Clarke, Ryan M. and Zheng, Shao-Liang and Cundari, Thomas R. and Betley, Theodore A.},
abstractNote = {The trityl-substituted bisoxazoline (TrHBOX) was prepared as a chiral analogue to a previously reported nickel dipyrrin system capable of ring-closing amination catalysis. Ligand metalation with divalent NiI2(py)4 followed by potassium graphite reduction afforded the monovalent (TrHBOX)Ni(py) (4). Slow addition of 1.4 equiv of a benzene solution of 1-adamantylazide to 4 generated the tetrazido (TrHBOX)Ni(κ2-N4Ad2) (5) and terminal iminyl adduct (TrHBOX)Ni(NAd) (6). Investigation of 6 via single-crystal X-ray crystallography, NMR and EPR spectroscopies, and computations revealed a Ni(II)-iminyl radical formulation, similar to its dipyrrinato congener. Complex 4 exhibits enantioselective intramolecular C–H bond amination to afford N-heterocyclic products from 4-aryl-2-methyl-2-azidopentanes. Catalytic C–H amination occurs under mild conditions (5 mol % catalyst, 60 °C) and provides pyrrolidine products in decent yield (29%–87%) with moderate ee (up to 73%). Substrates with a 3,5-dialkyl substitution on the 4-aryl position maximized the observed enantioselectivity. Kinetic studies to probe the reaction mechanism were conducted using 1H and 19F NMR spectroscopies. A small, intermolecular kinetic isotope effect (1.35 ± 0.03) suggests an H-atom abstraction step with an asymmetric transition state while the reaction rate is measured to be first order in catalyst and zeroth order in substrate concentrations. Enantiospecific deuterium labeling studies show that the enantioselectivity is dictated by both the H-atom abstraction and radical recombination steps due to the comparable rate between radical rotation and C–N bond formation. Furthermore, the competing elements of the two-step reaction where H-removal from the pro-R configuration is preferred while the preferential radical capture occurs with the Si face of the carboradical likely lead to the diminished ee observed, as corroborated by theoretical calculations. Furthermore, based on these enantio-determining steps, catalytic enantioselective synthesis of 2,5-bis-tertiary pyrrolidines is demonstrated with good yield (50–78%) and moderate ee (up to 79%).},
doi = {10.1021/jacs.0c09839},
journal = {Journal of the American Chemical Society},
number = 2,
volume = 143,
place = {United States},
year = {Mon Jan 04 00:00:00 EST 2021},
month = {Mon Jan 04 00:00:00 EST 2021}
}
Copy to clipboard
Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1021/jacs.0c09839
Copyright Statement
Other availability
Search WorldCat Search WorldCat to find libraries that may hold this journal
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:

Privileged Structures Meet Human T-Cell Leukemia Virus-1 (HTLV-1): C 2 -Symmetric 3,4-Disubstituted Pyrrolidines as Nonpeptidic HTLV-1 Protease Inhibitors
journal, May 2015

Synthesis, characterization and C–H amination reactivity of nickel iminyl complexes
journal, January 2020

  • Dong, Yuyang; Lukens, James T.; Clarke, Ryan M.
  • Chemical Science, Vol. 11, Issue 5
  • DOI: 10.1039/C9SC04879K

C–H Functionalization Reactivity of a Nickel–Imide
journal, June 2012

  • Wiese, Stefan; McAfee, Jason L.; Pahls, Dale R.
  • Journal of the American Chemical Society, Vol. 134, Issue 24
  • DOI: 10.1021/ja302149k

Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis
journal, November 2017

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals: Miniperspective
journal, October 2014

  • Vitaku, Edon; Smith, David T.; Njardarson, Jon T.
  • Journal of Medicinal Chemistry, Vol. 57, Issue 24
  • DOI: 10.1021/jm501100b

A New Sparteine Surrogate for Asymmetric Deprotonation of N -Boc Pyrrolidine
journal, March 2008

  • Stead, Darren; O'Brien, Peter; Sanderson, Adam
  • Organic Letters, Vol. 10, Issue 7
  • DOI: 10.1021/ol800109s

Iron bis(oxazoline) complexes in asymmetric catalysis
journal, January 2016

  • Ollevier, Thierry
  • Catalysis Science & Technology, Vol. 6, Issue 1
  • DOI: 10.1039/C5CY01357G

Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines
journal, May 2008

  • Allen, Damian A.; Tomaso, Anthony E.; Priest, Owen P.
  • Journal of Chemical Education, Vol. 85, Issue 5
  • DOI: 10.1021/ed085p698

Tautomerism in Bis(oxazoline)s: Tautomerism in Bis(oxazoline)s
journal, October 2013

  • Walli, Adam; Dechert, Sebastian; Meyer, Franc
  • European Journal of Organic Chemistry, Vol. 2013, Issue 31
  • DOI: 10.1002/ejoc.201301282

Stereochemistry of the Singlet Oxygenation of Simple Alkenes: A Stereospecific Transformation
journal, August 2008

  • Alberti, Mariza N.; Vassilikogiannakis, Georgios; Orfanopoulos, Michael
  • Organic Letters, Vol. 10, Issue 18
  • DOI: 10.1021/ol801488w

Direct Comparison of C–H Bond Amination Efficacy through Manipulation of Nitrogen-Valence Centered Redox: Imido versus Iminyl
journal, October 2017

  • Wilding, Matthew J. T.; Iovan, Diana A.; Wrobel, Alexandra T.
  • Journal of the American Chemical Society, Vol. 139, Issue 41
  • DOI: 10.1021/jacs.7b08714

Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis
journal, August 1980

  • Vosko, S. H.; Wilk, L.; Nusair, M.
  • Canadian Journal of Physics, Vol. 58, Issue 8
  • DOI: 10.1139/p80-159

Rh 2 (II,III) Catalysts with Chelating Carboxylate and Carboxamidate Supports: Electronic Structure and Nitrene Transfer Reactivity
journal, February 2016

  • Varela-Álvarez, Adrián; Yang, Tzuhsiung; Jennings, Heather
  • Journal of the American Chemical Society, Vol. 138, Issue 7
  • DOI: 10.1021/jacs.5b12790

Rings in Drugs: Miniperspective
journal, February 2014

  • Taylor, Richard D.; MacCoss, Malcolm; Lawson, Alastair D. G.
  • Journal of Medicinal Chemistry, Vol. 57, Issue 14
  • DOI: 10.1021/jm4017625

Complex N-Heterocycle Synthesis via Iron-Catalyzed, Direct C-H Bond Amination
journal, May 2013

Enantioselective, Palladium-Catalyzed α-Arylation of N -Boc-pyrrolidine
journal, March 2006

  • Campos, Kevin R.; Klapars, Artis; Waldman, Jacob H.
  • Journal of the American Chemical Society, Vol. 128, Issue 11
  • DOI: 10.1021/ja0605265

Catalytic Synthesis of N-Heterocycles via Direct C(sp 3 )–H Amination Using an Air-Stable Iron(III) Species with a Redox-Active Ligand
journal, March 2017

  • Bagh, Bidraha; Broere, Daniël L. J.; Sinha, Vivek
  • Journal of the American Chemical Society, Vol. 139, Issue 14
  • DOI: 10.1021/jacs.7b00270

C 2 -Symmetric Chiral Bis(Oxazoline) Ligands in Asymmetric Catalysis
journal, August 2006

  • Desimoni, Giovanni; Faita, Giuseppe; Jørgensen, Karl Anker
  • Chemical Reviews, Vol. 106, Issue 9
  • DOI: 10.1021/cr0505324

Transition-Metal-Catalyzed Reactions in Heterocyclic Synthesis
journal, May 2004

  • Nakamura, Itaru; Yamamoto, Yoshinori
  • Chemical Reviews, Vol. 104, Issue 5
  • DOI: 10.1021/cr020095i

A complete basis set model chemistry. I. The total energies of closed‐shell atoms and hydrides of the first‐row elements
journal, August 1988

  • Petersson, G. A.; Bennett, Andrew; Tensfeldt, Thomas G.
  • The Journal of Chemical Physics, Vol. 89, Issue 4
  • DOI: 10.1063/1.455064

Synthesis of Aziridines from Alkenes and Aryl Azides with a Reusable Macrocyclic Tetracarbene Iron Catalyst
journal, December 2011

  • Cramer, S. Alan; Jenkins, David M.
  • Journal of the American Chemical Society, Vol. 133, Issue 48
  • DOI: 10.1021/ja2090965

Stereochemical Probes of Intramolecular C−H Insertion Reactions of Iron-Carbene Complexes
journal, June 2000

  • Ishii, Shingo; Zhao, Shikai; Helquist, Paul
  • Journal of the American Chemical Society, Vol. 122, Issue 24
  • DOI: 10.1021/ja000239f

Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications
journal, January 2017

Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles
journal, February 2019

  • Dai, Xi-Jie; Engl, Oliver D.; León, Thierry
  • Angewandte Chemie International Edition, Vol. 58, Issue 11
  • DOI: 10.1002/anie.201814331

.alpha.-Methoxy-.alpha.-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
journal, September 1969

  • Dale, James A.; Dull, David L.; Mosher, Harry S.
  • The Journal of Organic Chemistry, Vol. 34, Issue 9
  • DOI: 10.1021/jo01261a013

A Novel ( R )-Imine Reductase from Paenibacillus lactis for Asymmetric Reduction of 3  H -Indoles
journal, January 2016

A Terminal Ni(III)−Imide with Diverse Reactivity Pathways
journal, August 2005

  • Kogut, Elzbieta; Wiencko, Heather L.; Zhang, Libei
  • Journal of the American Chemical Society, Vol. 127, Issue 32
  • DOI: 10.1021/ja0533186

Fully optimized contracted Gaussian basis sets for atoms Li to Kr
journal, August 1992

  • Schäfer, Ansgar; Horn, Hans; Ahlrichs, Reinhart
  • The Journal of Chemical Physics, Vol. 97, Issue 4
  • DOI: 10.1063/1.463096

Stereoselectivity and Structural Characterization of an Imine Reductase (IRED) from Amycolatopsis orientalis
journal, May 2016

Ligand–Substrate Dispersion Facilitates the Copper-Catalyzed Hydroamination of Unactivated Olefins
journal, November 2017

  • Lu, Gang; Liu, Richard Y.; Yang, Yang
  • Journal of the American Chemical Society, Vol. 139, Issue 46
  • DOI: 10.1021/jacs.7b07373

Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements
journal, October 1982

  • Francl, Michelle M.; Pietro, William J.; Hehre, Warren J.
  • The Journal of Chemical Physics, Vol. 77, Issue 7, p. 3654-3665
  • DOI: 10.1063/1.444267

Enantiomerically pure (R)-(+)-2-phenylethanol-2-d and -1,1,2-d3, and (S)-(+)-1-phenylethane-1-d, -1,2,-d2, -1,2,2-d3, and -1,2,2,2-d4
journal, February 1979

  • Elsenbaumer, Ronald L.; Mosher, Harry S.
  • The Journal of Organic Chemistry, Vol. 44, Issue 4
  • DOI: 10.1021/jo01318a024

Characterization of Iron-Imido Species Relevant for N -Group Transfer Chemistry
journal, February 2016

  • Iovan, Diana A.; Betley, Theodore A.
  • Journal of the American Chemical Society, Vol. 138, Issue 6
  • DOI: 10.1021/jacs.5b12582

Orthoesters and Related Compounds from Malono- and Succinonitriles
journal, January 1949

  • McElvain, S. M.; Schroeder, Juel P.
  • Journal of the American Chemical Society, Vol. 71, Issue 1
  • DOI: 10.1021/ja01169a013

Synthesis of chiral cyclic amines via Ir-catalyzed enantioselective hydrogenation of cyclic imines
journal, January 2017

  • Zhang, Ying; Kong, Duanyang; Wang, Rui
  • Organic & Biomolecular Chemistry, Vol. 15, Issue 14
  • DOI: 10.1039/C7OB00442G

Robust and Porous β-Diketiminate-Functionalized Metal–Organic Frameworks for Earth-Abundant-Metal-Catalyzed C–H Amination and Hydrogenation
journal, March 2016

  • Thacker, Nathan C.; Lin, Zekai; Zhang, Teng
  • Journal of the American Chemical Society, Vol. 138, Issue 10
  • DOI: 10.1021/jacs.5b13394

High-Spin Iron Imido Complexes Competent for C–H Bond Amination
journal, August 2017

  • Wilding, Matthew J. T.; Iovan, Diana A.; Betley, Theodore A.
  • Journal of the American Chemical Society, Vol. 139, Issue 34
  • DOI: 10.1021/jacs.7b06682

Mechanism of Cobalt(II) Porphyrin-Catalyzed C–H Amination with Organic Azides: Radical Nature and H-Atom Abstraction Ability of the Key Cobalt(III)–Nitrene Intermediates
journal, August 2011

  • Lyaskovskyy, Volodymyr; Suarez, Alma I. Olivos; Lu, Hongjian
  • Journal of the American Chemical Society, Vol. 133, Issue 31
  • DOI: 10.1021/ja204800a

6-31G * basis set for atoms K through Zn
journal, July 1998

  • Rassolov, Vitaly A.; Pople, John A.; Ratner, Mark A.
  • The Journal of Chemical Physics, Vol. 109, Issue 4
  • DOI: 10.1063/1.476673

3d Transition Metals for C–H Activation
journal, October 2018

Effect of Ligand Structure in the Bisoxazoline Mediated Asymmetric Addition of Methyllithium to Imines
journal, August 2000

  • Denmark, Scott E.; Stiff, Cory M.
  • The Journal of Organic Chemistry, Vol. 65, Issue 18
  • DOI: 10.1021/jo0007175

Density‐functional thermochemistry. III. The role of exact exchange
journal, April 1993

  • Becke, Axel D.
  • The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652
  • DOI: 10.1063/1.464913

Stereochemical dynamics of aliphatic hydroxylation by cytochrome P-450
journal, September 1986

  • White, Ronald E.; Miller, John P.; Favreau, Leonard V.
  • Journal of the American Chemical Society, Vol. 108, Issue 19
  • DOI: 10.1021/ja00279a059

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
journal, January 1988

η 2 -Organoazide Complexes of Nickel and Their Conversion to Terminal Imido Complexes via Dinitrogen Extrusion
journal, September 2008

  • Waterman, Rory; Hillhouse, Gregory L.
  • Journal of the American Chemical Society, Vol. 130, Issue 38
  • DOI: 10.1021/ja805530z

Characteristic Conformation of Mosher’s Amide Elucidated Using the Cambridge Structural Database
journal, July 2015

Iridium-Catalyzed Asymmetric Hydrosilylation of Imines Using Chiral Oxazolinyl-Phosphine Ligands
journal, April 1999

  • Takei, Izuru; Nishibayashi, Yoshiaki; Arikawa, Yasuyoshi
  • Organometallics, Vol. 18, Issue 11
  • DOI: 10.1021/om981005w

Efficient C–H Amination Catalysis Using Nickel-Dipyrrin Complexes
journal, May 2020

  • Dong, Yuyang; Clarke, Ryan M.; Porter, Gerard J.
  • Journal of the American Chemical Society, Vol. 142, Issue 25
  • DOI: 10.1021/jacs.0c02126

Synthesis and Characterization of Three-Coordinate Ni(III)-Imide Complexes
journal, August 2011

  • Iluc, Vlad M.; Miller, Alexander J. M.; Anderson, John S.
  • Journal of the American Chemical Society, Vol. 133, Issue 33
  • DOI: 10.1021/ja2024993

Bis(oxazolines) as chiral ligands in metal-catalyzed asymmetric reactions. Catalytic, asymmetric cyclopropanation of olefins
journal, January 1991

  • Evans, David A.; Woerpel, Keith A.; Hinman, Mira M.
  • Journal of the American Chemical Society, Vol. 113, Issue 2, p. 726-728
  • DOI: 10.1021/ja00002a080

C2-Symmetric chiral bis(oxazoline)–metal complexes in catalytic asymmetric synthesis
journal, January 1998

Preparation of Chiral Bisoxazolines: Observations on the Effect of Substituents
journal, July 1995

  • Denmark, Scott E.; Nakajima, Noriyuki; Nicaise, Olivier J. -C.
  • The Journal of Organic Chemistry, Vol. 60, Issue 15
  • DOI: 10.1021/jo00120a036

Rotational barriers in alkanes
journal, February 2011

  • Mo, Yirong
  • WIREs Computational Molecular Science, Vol. 1, Issue 2
  • DOI: 10.1002/wcms.22

Asymmetric Induction and Enantiodivergence in Catalytic Radical C–H Amination via Enantiodifferentiative H-Atom Abstraction and Stereoretentive Radical Substitution
journal, July 2019

  • Lang, Kai; Torker, Sebastian; Wojtas, Lukasz
  • Journal of the American Chemical Society, Vol. 141, Issue 31
  • DOI: 10.1021/jacs.9b05850

A reductive aminase from Aspergillus oryzae
journal, May 2017

  • Aleku, Godwin A.; France, Scott P.; Man, Henry
  • Nature Chemistry, Vol. 9, Issue 10
  • DOI: 10.1038/nchem.2782

A Model “Rebound” Mechanism of Hydroxylation by Cytochrome P450:  Stepwise and Effectively Concerted Pathways, and Their Reactivity Patterns
journal, September 2000

  • Ogliaro, François; Harris, Nathan; Cohen, Shimrit
  • Journal of the American Chemical Society, Vol. 122, Issue 37
  • DOI: 10.1021/ja991878x

Direct Manipulation of Metal Imido Geometry: Key Principles to Enhance C–H Amination Efficacy
journal, September 2019

  • Baek, Yunjung; Hennessy, Elisabeth T.; Betley, Theodore A.
  • Journal of the American Chemical Society, Vol. 141, Issue 42
  • DOI: 10.1021/jacs.9b09015

Terminal Amido and Imido Complexes of Three-Coordinate Nickel
journal, May 2001

  • Mindiola, Daniel J.; Hillhouse, Gregory L.
  • Journal of the American Chemical Society, Vol. 123, Issue 19
  • DOI: 10.1021/ja010358a

Strongly bent nickel imides supported by a chelating bis(N-heterocyclic carbene) ligand
journal, January 2013

  • Harrold, Nicole D.; Hillhouse, Gregory L.
  • Chemical Science, Vol. 4, Issue 10
  • DOI: 10.1039/c3sc51517f

Sequence‐Based In‐silico Discovery, Characterisation, and Biocatalytic Application of a Set of Imine Reductases
journal, July 2018

  • Velikogne, Stefan; Resch, Verena; Dertnig, Carina
  • ChemCatChem, Vol. 10, Issue 15
  • DOI: 10.1002/cctc.201800607

Highly Enantioselective Imine Hydrosilylation Using ( S,S )-Ethylenebis(η 5 -tetrahydroindenyl)titanium Difluoride
journal, January 1996

  • Verdaguer, Xavier; Lange, Udo E. W.; Reding, Matthew T.
  • Journal of the American Chemical Society, Vol. 118, Issue 28
  • DOI: 10.1021/ja960808c

A complete basis set model chemistry. II. Open‐shell systems and the total energies of the first‐row atoms
journal, May 1991

  • Petersson, G. A.; Al‐Laham, Mohammad A.
  • The Journal of Chemical Physics, Vol. 94, Issue 9
  • DOI: 10.1063/1.460447

Characterization of Porphyrin-Co(III)-‘Nitrene Radical’ Species Relevant in Catalytic Nitrene Transfer Reactions
journal, April 2015

  • Goswami, Monalisa; Lyaskovskyy, Volodymyr; Domingos, Sérgio R.
  • Journal of the American Chemical Society, Vol. 137, Issue 16
  • DOI: 10.1021/jacs.5b01197

Enantioselective intramolecular C–H amination of aliphatic azides by dual ruthenium and phosphine catalysis
journal, January 2019

  • Qin, Jie; Zhou, Zijun; Cui, Tianjiao
  • Chemical Science, Vol. 10, Issue 11
  • DOI: 10.1039/C9SC00054B

Asymmetric synthesis of 2-substituted pyrrolidines by addition of Grignard reagents to γ-chlorinated N-tert-butanesulfinyl imine
journal, January 2010

  • Reddy, Leleti Rajender; Prashad, Mahavir
  • Chem. Commun., Vol. 46, Issue 2
  • DOI: 10.1039/B917435D

An Effective [Fe III (TF 4 DMAP)Cl] Catalyst for C–H Bond Amination with Aryl and Alkyl Azides
journal, February 2019

On the Interpretation of Deuterium Kinetic Isotope Effects in CH Bond Functionalizations by Transition-Metal Complexes
journal, March 2012

  • Simmons, Eric M.; Hartwig, John F.
  • Angewandte Chemie International Edition, Vol. 51, Issue 13
  • DOI: 10.1002/anie.201107334

Nitrene Radical Intermediates in Catalytic Synthesis
journal, September 2017

  • Kuijpers, Petrus F.; van der Vlugt, Jarl Ivar; Schneider, Sven
  • Chemistry - A European Journal, Vol. 23, Issue 56
  • DOI: 10.1002/chem.201702537

EasySpin, a comprehensive software package for spectral simulation and analysis in EPR
journal, January 2006

Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr
journal, April 1994

  • Schäfer, Ansgar; Huber, Christian; Ahlrichs, Reinhart
  • The Journal of Chemical Physics, Vol. 100, Issue 8
  • DOI: 10.1063/1.467146

N-Heterocyclic Carbene Iron(III) Porphyrin-Catalyzed Intramolecular C(sp 3 )-H Amination of Alkyl Azides
journal, August 2018

  • Shing, Ka-Pan; Liu, Yungen; Cao, Bei
  • Angewandte Chemie International Edition, Vol. 57, Issue 37
  • DOI: 10.1002/anie.201806059

Catalytic C–H Amination Mediated by Dipyrrin Cobalt Imidos
journal, April 2019

  • Baek, Yunjung; Betley, Theodore A.
  • Journal of the American Chemical Society, Vol. 141, Issue 19
  • DOI: 10.1021/jacs.9b01262

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

Cobalt-Porphyrin-Catalysed Intramolecular Ring-Closing C−H Amination of Aliphatic Azides: A Nitrene-Radical Approach to Saturated Heterocycles
journal, May 2017

  • Kuijpers, Petrus F.; Tiekink, Martijn J.; Breukelaar, Willem B.
  • Chemistry - A European Journal, Vol. 23, Issue 33
  • DOI: 10.1002/chem.201700358

Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields
journal, November 1994

  • Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.
  • The Journal of Physical Chemistry, Vol. 98, Issue 45, p. 11623-11627
  • DOI: 10.1021/j100096a001

Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides
journal, January 2019

  • Adrio, Javier; Carretero, Juan C.
  • Chemical Communications, Vol. 55, Issue 80
  • DOI: 10.1039/C9CC05238K

Probing the role of an Fe IV tetrazene in catalytic aziridination
journal, January 2014

  • Cramer, S. Alan; Hernández Sánchez, Raúl; Brakhage, Desirae F.
  • Chem. Commun., Vol. 50, Issue 90
  • DOI: 10.1039/C4CC05124F

Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination
journal, September 2019

N-tert -Butanesulfinyl Imines:  Versatile Intermediates for the Asymmetric Synthesis of Amines
journal, August 2002

  • Ellman, Jonathan A.; Owens, Timothy D.; Tang, Tony P.
  • Accounts of Chemical Research, Vol. 35, Issue 11
  • DOI: 10.1021/ar020066u
    Sort by:
    [ × clear filter / sort ]

    Similar Records in DOE PAGES and OSTI.GOV collections:

    Other research related to this record: