Review
Complexes with Nitrogen‐Centered Radical Ligands: Classification, Spectroscopic Features, Reactivity, and Catalytic Applications
Abstract
The electronic structure, spectroscopic features, and (catalytic) reactivity of complexes with nitrogen‐centered radical ligands are described. Complexes with aminyl ([M(.NR2)]), nitrene/imidyl ([M(.NR)]), and nitridyl radical ligands ([M(.N)]) are detectable and sometimes even isolable species, and despite their radical nature frequently reveal selective reactivity patterns towards a variety of organic substrates. A classification system for complexes with nitrogen‐centered radical ligands based on their electronic structure leads to their description as one‐electron‐reduced Fischer‐type systems, one‐electron‐oxidized Schrock‐type systems, or systems with a (nearly) covalent MN π bond. Experimental data relevant for the assignment of the radical locus (i.e. metal or ligand) are discussed, and the application of complexes with nitrogen‐centered radical ligands in the (catalytic) syntheses of nitrogen‐containing organic molecules such as aziridines and amines is demonstrated with recent examples. This Review should contribute to a better understanding of the (catalytic) reactivity of nitrogen‐centered radical ligands and the role they play in tuning the reactivity of coordination compounds.
Citing Literature
Number of times cited: 89
- Yufeng Ren, Khaled Cheaib, Jérémy Jacquet, Hervé Vezin, Louis Fensterbank, Maylis Orio, Sébastien Blanchard and Marine Desage‐El Murr, Copper‐Catalyzed Aziridination with Redox‐Active Ligands: Molecular Spin Catalysis, Chemistry – A European Journal, 24, 20, (5086-5090), (2018).
- Ruben B. Richrath, Theresa Olyschläger, Sven Hildebrandt, Daniel G. Enny, Godfred D. Fianu, Robert A. Flowers and Andreas Gansäuer, Cp2TiX Complexes for Sustainable Catalysis in Single‐Electron Steps, Chemistry – A European Journal, 24, 24, (6371-6379), (2018).
- Igor L. Fedushkin, Vladimir A. Dodonov, Alexandra A. Skatova, Vladimir G. Sokolov, Alexander V. Piskunov and Georgii K. Fukin, Redox‐Active Ligand‐Assisted Two‐Electron Oxidative Addition to Gallium(II), Chemistry � A European Journal, 24, 8, (1877-1889), (2018).
- Petrus F. Kuijpers, Jarl Ivar van der Vlugt, Sven Schneider and Bas de Bruin, Nitrene Radical Intermediates in Catalytic Synthesis, Chemistry – A European Journal, 23, 56, (13819-13829), (2017).
- Kirill Yu. Monakhov, Jan van Leusen, Paul Kögerler, Emilie‐Laure Zins, M. Esmaïl Alikhani, Moniek Tromp, Andreas A. Danopoulos and Pierre Braunstein, Linear, Trinuclear Cobalt Complexes with o‐Phenylene‐bis‐Silylamido Ligands, Chemistry – A European Journal, 23, 27, (6504-6508), (2017).
- Abolghasem (Gus) Bakhoda, Quan Jiang, Jeffery A. Bertke, Thomas R. Cundari and Timothy H. Warren, Elusive Terminal Copper Arylnitrene Intermediates, Angewandte Chemie International Edition, 56, 23, (6426-6430), (2017).
- Rafael E. Rodríguez‐Lugo, Bas de Bruin, Monica Trincado and Hansjörg Grützmacher, A Stable Aminyl Radical Coordinated to Cobalt, Chemistry – A European Journal, 23, 28, (6795-6802), (2017).
- Vincent Vreeken, Maxime A. Siegler and Jarl Ivar van der Vlugt, Controlled Interconversion of a Dinuclear Au Species Supported by a Redox‐Active Bridging PNP Ligand Facilitates Ligand‐to‐Gold Electron Transfer, Chemistry – A European Journal, 23, 23, (5585-5594), (2017).
- Petrus F. Kuijpers, Martijn J. Tiekink, Willem B. Breukelaar, Daniël L. J. Broere, Nicolaas P. van Leest, Jarl Ivar van der Vlugt, Joost N. H. Reek and Bas de Bruin, Cobalt‐Porphyrin‐Catalysed Intramolecular Ring‐Closing C−H Amination of Aliphatic Azides: A Nitrene‐Radical Approach to Saturated Heterocycles, Chemistry – A European Journal, 23, 33, (7945-7952), (2017).
- Abolghasem (Gus) Bakhoda, Quan Jiang, Jeffery A. Bertke, Thomas R. Cundari and Timothy H. Warren, Elusive Terminal Copper Arylnitrene Intermediates, Angewandte Chemie, 129, 23, (6526-6530), (2017).
- T Ishida, Spin-Parity Behavior in the Exchange-Coupled Lanthanoid-Nitroxide Molecular Magnets, IOP Conference Series: Materials Science and Engineering, 202, (012001), (2017).
- Huiling Jiang, Kai Lang, Hongjian Lu, Lukasz Wojtas and X. Peter Zhang, Asymmetric Radical Bicyclization of Allyl Azidoformates via Cobalt(II)-Based Metalloradical Catalysis, Journal of the American Chemical Society, 10.1021/jacs.7b05778, 139, 27, (9164-9167), (2017).
- Suvendu Maity, Suman Kundu, Sandip Mondal, Sachinath Bera and Prasanta Ghosh, Molecular and Electronic Structures of Ruthenium Complexes Containing an ONS-Coordinated Open-Shell π Radical and an Oxidative Aromatic Ring Cleavage Reaction, Inorganic Chemistry, 56, 6, (3363), (2017).
- Sima Roy, Shuvam Pramanik, Sarat Chandra Patra, Basab Adhikari, Abhishake Mondal, Sanjib Ganguly and Kausikisankar Pramanik, Ambient-Stable Bis-Azoaromatic-Centered Diradical [(L • )M(L • )] Complexes of Rh(III): Synthesis, Structure, Redox, and Spin–Spin Interaction , Inorganic Chemistry, 10.1021/acs.inorgchem.7b01514, 56, 21, (12764-12774), (2017).
- Xue Xu, Yong Wang, Xin Cui, Lukasz Wojtas and X. Peter Zhang, Metalloradical activation of α-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes, Chemical Science, 10.1039/C7SC00658F, 8, 6, (4347-4351), (2017).
- Zheng-Yang Gu, Yuan Liu, Fei Wang, Xiaoguang Bao, Shun-Yi Wang and Shun-Jun Ji, Cobalt(II)-Catalyzed Synthesis of Sulfonyl Guanidines via Nitrene Radical Coupling with Isonitriles: A Combined Experimental and Computational Study, ACS Catalysis, 7, 6, (3893), (2017).
- V. Vreeken, L. Baij, B. de Bruin, M. A. Siegler and J. I. van der Vlugt, N-Atom transfer via thermal or photolytic activation of a Co-azido complex with a PNP pincer ligand, Dalton Trans., 10.1039/C7DT01712J, 46, 22, (7145-7149), (2017).
- Claudia Kleinlein, Shao-Liang Zheng and Theodore A. Betley, Ground State and Excited State Tuning in Ferric Dipyrrin Complexes Promoted by Ancillary Ligand Exchange, Inorganic Chemistry, 10.1021/acs.inorgchem.7b00525, 56, 10, (5892-5901), (2017).
- Hao Tang, Edward N. Brothers and Michael B. Hall, The Distinctive Electronic Structures of Rhenium Tris(thiolate) Complexes, an Unexpected Contrast to the Valence Isoelectronic Ruthenium Tris(thiolate) Complexes, Inorganic Chemistry, 10.1021/acs.inorgchem.6b02434, 56, 1, (583-593), (2016).
- Lianrui Hu and Hui Chen, What Factors Control the Reactivity of Cobalt–Imido Complexes in C–H Bond Activation via Hydrogen Abstraction?, ACS Catalysis, 10.1021/acscatal.6b02694, 7, 1, (285-292), (2016).
- Nicolas Leconte, Jules Moutet, Khrystyna Herasymchuk, Ryan M. Clarke, Christian Philouze, Dominique Luneau, Tim Storr and Fabrice Thomas, Mn( iv ) and Mn( v )-radical species supported by the redox non-innocent bis(2-amino-3,5-di-tert-butylphenyl)amine pincer ligand , Chem. Commun., 10.1039/C7CC00516D, 53, 18, (2764-2767), (2017).
- Yong Wang, Xin Wen, Xin Cui, Lukasz Wojtas and X. Peter Zhang, Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis, Journal of the American Chemical Society, 10.1021/jacs.6b11336, 139, 3, (1049-1052), (2017).
- Lucie Nurdin, Denis M. Spasyuk, Warren E. Piers and Laurent Maron, Reactions of Neutral Cobalt(II) Complexes of a Dianionic Tetrapodal Pentadentate Ligand: Cobalt(III) Amides from Imido Radicals, Inorganic Chemistry, 56, 7, (4157), (2017).
- Matthew J. T. Wilding, Diana A. Iovan, Alexandra T. Wrobel, James T. Lukens, Samantha N. MacMillan, Kyle M. Lancaster and Theodore A. Betley, Direct Comparison of C–H Bond Amination Efficacy through Manipulation of Nitrogen-Valence Centered Redox: Imido versus Iminyl, Journal of the American Chemical Society, 10.1021/jacs.7b08714, 139, 41, (14757-14766), (2017).
- Samantha N. MacMillan and Kyle M. Lancaster, X-ray Spectroscopic Interrogation of Transition-Metal-Mediated Homogeneous Catalysis: Primer and Case Studies, ACS Catalysis, 10.1021/acscatal.6b02875, 7, 3, (1776-1791), (2017).
- Bidraha Bagh, Daniël L. J. Broere, Vivek Sinha, Petrus F. Kuijpers, Nicolaas P. van Leest, Bas de Bruin, Serhiy Demeshko, Maxime A. Siegler and Jarl Ivar van der Vlugt, 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 of the American Chemical Society, 10.1021/jacs.7b00270, 139, 14, (5117-5124), (2017).
- Luca Legnani and Bill Morandi, Direct Catalytic Synthesis of Unprotected 2‐Amino‐1‐Phenylethanols from Alkenes by Using Iron(II) Phthalocyanine, Angewandte Chemie International Edition, 55, 6, (2248-2251), (2016).
- Zheng Huang and Jean‐Philip Lumb, A Catalyst‐Controlled Aerobic Coupling of ortho‐Quinones and Phenols Applied to the Synthesis of Aryl Ethers, Angewandte Chemie International Edition, 55, 38, (11543-11547), (2016).
- Luca Legnani and Bill Morandi, , Angewandte Chemie, 128, 6, (2288-2292), (2016).
- Zheng Huang and Jean‐Philip Lumb, A Catalyst‐Controlled Aerobic Coupling of ortho‐Quinones and Phenols Applied to the Synthesis of Aryl Ethers, Angewandte Chemie, 128, 38, (11715-11719), (2016).
- Bidraha Bagh, Daniël L. J. Broere, Maxime A. Siegler and Jarl Ivar van der Vlugt, Redox‐Active‐Ligand‐Mediated Formation of an Acyclic Trinuclear Ruthenium Complex with Bridging Nitrido Ligands, Angewandte Chemie International Edition, 55, 29, (8381-8385), (2016).
- Huiling Jiang, Kai Lang, Hongjian Lu, Lukasz Wojtas and X. Peter Zhang, Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)‐Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures, Angewandte Chemie, 128, 38, (11776-11780), (2016).
- Bidraha Bagh, Daniël L. J. Broere, Maxime A. Siegler and Jarl Ivar van der Vlugt, Redox‐Active‐Ligand‐Mediated Formation of an Acyclic Trinuclear Ruthenium Complex with Bridging Nitrido Ligands, Angewandte Chemie, 128, 29, (8521-8525), (2016).
- Huiling Jiang, Kai Lang, Hongjian Lu, Lukasz Wojtas and X. Peter Zhang, Intramolecular Radical Aziridination of Allylic Sulfamoyl Azides by Cobalt(II)‐Based Metalloradical Catalysis: Effective Construction of Strained Heterobicyclic Structures, Angewandte Chemie International Edition, 55, 38, (11604-11608), (2016).
- Denis M. Spasyuk, Stephanie H. Carpenter, Christos E. Kefalidis, Warren E. Piers, Michael L. Neidig and Laurent Maron, Facile hydrogen atom transfer to iron( iii ) imido radical complexes supported by a dianionic pentadentate ligand , Chem. Sci., 10.1039/C6SC01433J, 7, 9, (5939-5944), (2016).
- Ewa Adela Miłopolska, Martin Kuss-Petermann, Markus Neuburger, Oliver Wenger and Thomas R. Ward, N -Heterocyclic carbene ligands bearing a naphthoquinone appendage: Synthesis and coordination chemistry, Polyhedron, 10.1016/j.poly.2015.04.019, 103, (261-266), (2016).
- John J. Kiernicki, Maryline G. Ferrier, Juan S. Lezama Pacheco, Henry S. La Pierre, Benjamin W. Stein, Matthias Zeller, Stosh A. Kozimor and Suzanne C. Bart, Examining the Effects of Ligand Variation on the Electronic Structure of Uranium Bis(imido) Species, Journal of the American Chemical Society, 138, 42, (13941), (2016).
- Marina González-Burgos, Angel Alegría, Arantxa Arbe, Juan Colmenero and José A. Pomposo, An unexpected route to aldehyde-decorated single-chain nanoparticles from azides, Polymer Chemistry, 7, 43, (6570), (2016).
- Sachinath Bera, Suvendu Maity, Thomas Weyhermüller and Prasanta Ghosh, Radical non-radical states of the [Ru(PIQ)] core in complexes (PIQ = 9,10-phenanthreneiminoquinone), Dalton Transactions, 10.1039/C6DT00091F, 45, 19, (8236-8247), (2016).
- P. Sutra and A. Igau, Anionic phosph(in)ito (“phosphoryl”) ligands: Non-classical “actor” phosphane-type ligands in coordination chemistry, Coordination Chemistry Reviews, 10.1016/j.ccr.2015.07.002, 308, (97-116), (2016).
- Ryan M. Clarke and Tim Storr, Tuning Electronic Structure To Control Manganese Nitride Activation, Journal of the American Chemical Society, 10.1021/jacs.6b09576, 138, 47, (15299-15302), (2016).
- Hinako Kawakami, Asato Tonegawa and Takayuki Ishida, A designed room-temperature triplet ligand from pyridine-2,6-diyl bis(tert-butyl nitroxide), Dalton Transactions, 10.1039/C5DT04218F, 45, 4, (1306-1309), (2016).
- Yihua Sun, Hao Tang, Kejuan Chen, Lianrui Hu, Jiannian Yao, Sason Shaik and Hui Chen, Two-State Reactivity in Low-Valent Iron-Mediated C–H Activation and the Implications for Other First-Row Transition Metals, Journal of the American Chemical Society, 10.1021/jacs.5b12150, 138, 11, (3715-3730), (2016).
- Christopher R. Benson, Elisabeth M. Fatila, Semin Lee, Matthew G. Marzo, Maren Pink, Michelle B. Mills, Kathryn E. Preuss and Amar H. Flood, Extreme Stabilization and Redox Switching of Organic Anions and Radical Anions by Large-Cavity, CH Hydrogen-Bonding Cyanostar Macrocycles, Journal of the American Chemical Society, 10.1021/jacs.6b09459, 138, 45, (15057-15065), (2016).
- Bas Bruin, Pauline Gualco and Nanda D. Paul, Redox Non‐innocent Ligands, Ligand Design in Metal Chemistry, (176-204), (2016).
- Jiaqiong Sun, Guangfan Zheng, Tao Xiong, Qiao Zhang, Jinbo Zhao, Yan Li and Qian Zhang, Copper-Catalyzed Hydroxyl-Directed Aminoarylation of Alkynes, ACS Catalysis, 6, 6, (3674), (2016).
- Tao Xiong and Qian Zhang, New amination strategies based on nitrogen-centered radical chemistry, Chemical Society Reviews, 45, 11, (3069), (2016).
- Xiaoyang Sun and Shouyun Yu, Visible-light-promoted iminyl radical formation from vinyl azides: synthesis of 6-(fluoro)alkylated phenanthridines, Chemical Communications, 10.1039/C6CC05756J, 52, 72, (10898-10901), (2016).
- Sachinath Bera, Suvendu Maity, Thomas Weyhermüller and Prasanta Ghosh, Arylamino radical complexes of ruthenium and osmium: dual radical counter in a molecule, Dalton Transactions, 10.1039/C6DT03728C, 45, 48, (19428-19440), (2016).
- Sachinath Bera, Sandip Mondal, Suvendu Maity, Thomas Weyhermüller and Prasanta Ghosh, Radical and Non-Radical States of the [Os(PIQ)] Core (PIQ = 9,10-Phenanthreneiminoquinone): Iminosemiquinone to Iminoquinone Conversion Promoted o -Metalation Reaction , Inorganic Chemistry, 10.1021/acs.inorgchem.6b00040, 55, 10, (4746-4756), (2016).
- T. Kikuchi, K. Kobayashi, K. Tsuge, S. Kitagawa and K. Tanaka, Asymmetric dimerization of aniline–ruthenium–dioxolene complex driven by stepwise PCET, Dalton Transactions, 10.1039/C6DT02573K, 45, 36, (14030-14034), (2016).
- Benjamin Eberle, Marko Damjanović, Markus Enders, Simone Leingang, Jessica Pfisterer, Christoph Krämer, Olaf Hübner, Elisabeth Kaifer and Hans-Jörg Himmel, Radical Monocationic Guanidino-Functionalized Aromatic Compounds (GFAs) as Bridging Ligands in Dinuclear Metal Acetate Complexes: Synthesis, Electronic Structure, and Magnetic Coupling, Inorganic Chemistry, 10.1021/acs.inorgchem.5b02614, 55, 4, (1683-1696), (2016).
- Ge Zhang, Tao Xiong, Zining Wang, Guoxing Xu, Xuedan Wang and Qian Zhang, Highly Regioselective Radical Amination of Allenes: Direct Synthesis of Allenamides and Tetrasubstituted Alkenes, Angewandte Chemie, 127, 43, (12840-12844), (2015).
- Ge Zhang, Tao Xiong, Zining Wang, Guoxing Xu, Xuedan Wang and Qian Zhang, Highly Regioselective Radical Amination of Allenes: Direct Synthesis of Allenamides and Tetrasubstituted Alkenes, Angewandte Chemie International Edition, 54, 43, (12649-12653), (2015).
- Mónica Trincado and Hansjörg Grützmacher, Cooperating Ligands in Catalysis, Cooperative Catalysis, (67-110), (2015).
- Spencer P. Heins, Wesley D. Morris, Peter T. Wolczanski, Emil B. Lobkovsky and Thomas R. Cundari, Nitrene Insertion into CC and CH Bonds of Diamide Diimine Ligands Ligated to Chromium and Iron, Angewandte Chemie International Edition, 54, 48, (14407-14411), (2015).
- Fabian Ehret, Martina Bubrin, Stanislav Záliš and Wolfgang Kaim, Metal‐Chelating N,N′‐Bis(4‐dimethylaminophenyl)acetamidinyl Radical: A New Chromophore for the Near‐Infrared Region, Chemistry – A European Journal, 21, 35, (12275-12278), (2015).
- Spencer P. Heins, Wesley D. Morris, Peter T. Wolczanski, Emil B. Lobkovsky and Thomas R. Cundari, Nitrene Insertion into CC and CH Bonds of Diamide Diimine Ligands Ligated to Chromium and Iron, Angewandte Chemie, 127, 48, (14615-14619), (2015).
- Vincent Vreeken, Maxime A. Siegler, Bas de Bruin, Joost N. H. Reek, Martin Lutz and Jarl Ivar van der Vlugt, CH Activation of Benzene by a Photoactivated NiII(azide): Formation of a Transient Nickel Nitrido Complex, Angewandte Chemie, 127, 24, (7161-7165), (2015).
- Vincent Vreeken, Maxime A. Siegler, Bas de Bruin, Joost N. H. Reek, Martin Lutz and Jarl Ivar van der Vlugt, CH Activation of Benzene by a Photoactivated NiII(azide): Formation of a Transient Nickel Nitrido Complex, Angewandte Chemie International Edition, 54, 24, (7055-7059), (2015).
- Madanakrishna Katari, Eleonore Payen de la Garanderie, Edith Nicol, Vincent Steinmetz, Guillaume van der Rest, Duncan Carmichael and Gilles Frison, Combining gas phase electron capture and IRMPD action spectroscopy to probe the electronic structure of a metastable reduced organometallic complex containing a non-innocent ligand, Physical Chemistry Chemical Physics, 10.1039/C5CP01501D, 17, 39, (25689-25692), (2015).
- Monalisa Goswami, Andrei Chirila, Christophe Rebreyend and Bas de Bruin, EPR Spectroscopy as a Tool in Homogeneous Catalysis Research, Topics in Catalysis, 58, 12-13, (719), (2015).
- Thorbjørn J. Morsing, Samantha N. MacMillan, Jacob W. H. Uebler, Theis Brock-Nannestad, Jesper Bendix and Kyle M. Lancaster, Stabilizing Coordinated Radicals via Metal–Ligand Covalency: A Structural, Spectroscopic, and Theoretical Investigation of Group 9 Tris(dithiolene) Complexes, Inorganic Chemistry, 10.1021/acs.inorgchem.5b00289, 54, 7, (3660-3669), (2015).
- Arne Glüer, Bjorn Askevold, Bastian Schluschaß, Frank W. Heinemann and Sven Schneider, Electron‐rich, Nitrido‐bridged Ruthenium Complexes, Zeitschrift f�r anorganische und allgemeine Chemie, 641, 1, (49-51), (2014).
- Selvan Demir, Ie-Rang Jeon, Jeffrey R. Long and T. David Harris, Radical ligand-containing single-molecule magnets, Coordination Chemistry Reviews, 10.1016/j.ccr.2014.10.012, 289-290, (149-176), (2015).
- Wei-juan Wang, Ting Zhang, Li-jun Duan, Xue-jing Zhang and Ming Yan, KOt-Bu promoted homocoupling and decomposition of N′-aryl acylhydrazines: synthesis of unsymmetric N′,N′-diaryl acylhydrazines, Tetrahedron, 71, 48, (9073), (2015).
- Brian M. Lindley, Peter T. Wolczanski, Thomas R. Cundari and Emil B. Lobkovsky, First-Row Transition Metal and Lithium Pyridine-ene-amide Complexes Exhibiting N- and C-Isomers and Ligand-Based Activation of Benzylic C–H Bonds, Organometallics, 10.1021/acs.organomet.5b00385, 34, 19, (4656-4668), (2015).
- Liangliang Zhou, Hong Yi, Lei Zhu, Xiaotian Qi, Hanpeng Jiang, Chao Liu, Yuqi Feng, Yu Lan and Aiwen Lei, Tuning the Reactivity of Radical through a Triplet Diradical Cu(II) Intermediate in Radical Oxidative Cross-Coupling, Scientific Reports, 10.1038/srep15934, 5, 1, (2015).
- Sinja Manck and Biprajit Sarkar, Use of EPR Spectroscopy to Unravel Reaction Mechanisms in (Catalytic) Bond Activation Reactions: Some Selected Examples, Topics in Catalysis, 58, 12-13, (751), (2015).
- Maria Besora, Ataualpa A.C. Braga, W.M.C. Sameera, Juan Urbano, Manuel R. Fructos, Pedro J. Pérez and Feliu Maseras, A computational view on the reactions of hydrocarbons with coinage metal complexes, Journal of Organometallic Chemistry, 10.1016/j.jorganchem.2014.10.009, 784, (2-12), (2015).
- Denan Wang, Sergey V. Lindeman and Adam T. Fiedler, Bimetallic Complexes Supported by a Redox-Active Ligand with Fused Pincer-Type Coordination Sites, Inorganic Chemistry, 10.1021/acs.inorgchem.5b01380, 54, 17, (8744-8754), (2015).
- Monalisa Goswami, Volodymyr Lyaskovskyy, Sérgio R. Domingos, Wybren Jan Buma, Sander Woutersen, Oliver Troeppner, Ivana Ivanović-Burmazović, Hongjian Lu, Xin Cui, X. Peter Zhang, Edward J. Reijerse, Serena DeBeer, Matti M. van Schooneveld, Florian Felix Pfaff, Kallol Ray and Bas de Bruin, Characterization of Porphyrin-Co(III)-‘Nitrene Radical’ Species Relevant in Catalytic Nitrene Transfer Reactions, Journal of the American Chemical Society, 10.1021/jacs.5b01197, 137, 16, (5468-5479), (2015).
- Markus G. Scheibel, Josh Abbenseth, Markus Kinauer, Frank W. Heinemann, Christian Würtele, Bas de Bruin and Sven Schneider, Homolytic N–H Activation of Ammonia: Hydrogen Transfer of Parent Iridium Ammine, Amide, Imide, and Nitride Species, Inorganic Chemistry, 10.1021/acs.inorgchem.5b00829, 54, 19, (9290-9302), (2015).
- Alma I. Olivos Suarez, Volodymyr Lyaskovskyy, Joost N. H. Reek, Jarl Ivar van der Vlugt and Bas de Bruin, ChemInform Abstract: Complexes with Nitrogen‐Centered Radical Ligands: Classification, Spectroscopic Features, Reactivity, and Catalytic Applications, ChemInform, 45, 6, (2014).
- Yann Gloaguen, Christophe Rebreyend, Martin Lutz, Pravin Kumar, Martina Huber, Jarl Ivar van der Vlugt, Sven Schneider and Bas de Bruin, An Isolated Nitridyl Radical‐Bridged {Rh(N.)Rh} Complex, Angewandte Chemie International Edition, 53, 26, (6814-6818), (2014).
- Yann Gloaguen, Christophe Rebreyend, Martin Lutz, Pravin Kumar, Martina Huber, Jarl Ivar van der Vlugt, Sven Schneider and Bas de Bruin, An Isolated Nitridyl Radical‐Bridged {Rh(N.)Rh} Complex, Angewandte Chemie, 126, 26, (6932-6936), (2014).
- Jan Breitenfeld, Matthew D. Wodrich and Xile Hu, Bimetallic Oxidative Addition in Nickel-Catalyzed Alkyl–Aryl Kumada Coupling Reactions, Organometallics, 33, 20, (5708), (2014).
- Daniël L. J. Broere, Bas de Bruin, Joost N. H. Reek, Martin Lutz, Sebastian Dechert and Jarl Ivar van der Vlugt, Intramolecular Redox-Active Ligand-to-Substrate Single-Electron Transfer: Radical Reactivity with a Palladium(II) Complex, Journal of the American Chemical Society, 10.1021/ja502164f, 136, 33, (11574-11577), (2014).
- Hideyuki Takisawa, Yui Morishima, Shoko Soma, Robert K. Szilagyi and Kiyoshi Fujisawa, Conversion of Carbon Dioxide to Oxalate by α-Ketocarboxylatocopper(II) Complexes, Inorganic Chemistry, 10.1021/ic5006242, 53, 16, (8191-8193), (2014).
- Ana M. Geer, Cristina Tejel, José A. López and Miguel A. Ciriano, Terminal Imido Rhodium Complexes, Angewandte Chemie, 126, 22, (5720-5724), (2014).
- Wen Zhou, Brian O. Patrick and Kevin M. Smith, Influence of redox non-innocent phenylenediamido ligands on chromium imido hydrogen-atom abstraction reactivity, Chem. Commun., 10.1039/C4CC04545A, 50, 69, (9958-9960), (2014).
- Kui-Hua Yang, Synthesis, crystal structures, and catalytic oxidation properties of oxidovanadium(V) complexes with Schiff base ligands, Transition Metal Chemistry, 10.1007/s11243-014-9821-1, 39, 4, (469-475), (2014).
- Ana M. Geer, Cristina Tejel, José A. López and Miguel A. Ciriano, Terminal Imido Rhodium Complexes, Angewandte Chemie International Edition, 53, 22, (5614-5618), (2014).
- Yu-Chang Chang, Wei-Chan Chang, Chan-Yu Hu and Fung-E Hong, Alkyl(quinolin-8-yl)phosphine Oxides as Hemilabile Preligands for Palladium-Catalyzed Reactions, Organometallics, 10.1021/om5004286, 33, 13, (3523-3534), (2014).
- Thomas Zell, Petr Milko, Kathlyn L. Fillman, Yael Diskin‐Posner, Tatyana Bendikov, Mark A. Iron, Gregory Leitus, Yehoshoa Ben‐David, Michael L. Neidig and David Milstein, Iron Dicarbonyl Complexes Featuring Bipyridine‐Based PNN Pincer Ligands with Short Interpyridine CC Bond Lengths: Innocent or Non‐Innocent Ligand?, Chemistry – A European Journal, 20, 15, (4403-4413), (2014).
- Nanda D. Paul, Sutanuva Mandal, Matthias Otte, Xin Cui, X. Peter Zhang and Bas de Bruin, Metalloradical Approach to 2 H -Chromenes , Journal of the American Chemical Society, 10.1021/ja4111336, 136, 3, (1090-1096), (2014).
- Markus G. Scheibel, Yanlin Wu, A. Claudia Stückl, Lennard Krause, Elena Carl, Dietmar Stalke, Bas de Bruin and Sven Schneider, Synthesis and Reactivity of a Transient, Terminal Nitrido Complex of Rhodium, Journal of the American Chemical Society, 10.1021/ja409764j, 135, 47, (17719-17722), (2013).
- Zheng‐Yang Gu, Rong Zhang, Shun‐Yi Wang and Shun‐Jun Ji, Cobalt(II)‐Catalyzed Bis‐isocyanides Insertion Reactions with Boric Acids and Sulfonyl Azides via Nitrene Radical Coupling, Chinese Journal of Chemistry, , (2018).
- Monalisa Goswami, Christophe Rebreyend and Bas de Bruin, Porphyrin Cobalt(III) “Nitrene Radical” Reactivity; Hydrogen Atom Transfer from Ortho-YH Substituents to the Nitrene Moiety of Cobalt-Bound Aryl Nitrene Intermediates (Y = O, NH), Molecules, 10.3390/molecules21020242, 21, 2, (242), (2016).
