Platz, M. S. in Reactive Intermediate Chemistry (eds Moss, R. A., Paztz, M. S. & Jones, M. Jr.), 501–559 (Wiley-VCH, 2003).
Dequirez, G., Pons, V. & Dauban, P. Nitrene chemistry in organic synthesis: still in its infancy? Angew. Chem. Int. Ed. 51, 7384–7395 (2012).
Tiemann, F. Ueber die einwirkung von benzolsulfonsäurechlorid auf amidoxime. Ber. Dtsch. Chem. Ges. 24, 4162–4167 (1891).
Meyer, D. M. & Roth, K. C. Discovery of interstellar NH. Astrophys. J. Lett. 376, L49–L52 (1991).
Wasserman, E. in Progress in Physical Organic Chemistry (eds Streitwieser, A. Jr. & Taft, R. W.), 319–336 (Wiley-VCH, 1971).
Gritsan, N. P. & Platz, M. S. Kinetics, spectroscopy, and computational chemistry of arylnitrenes. Chem. Rev. 106, 3844–3867 (2006).
Article CAS PubMed Google Scholar
Wentrup, C. Nitrenes, carbenes, diradicals, and ylides. Interconversions of reactive intermediates. Acc. Chem. Res. 44, 393–404 (2011).
Article CAS PubMed Google Scholar
Kvaskoff, D., Lüerssen, H., Bednarek, P. & Wentrup, C. Phenylnitrene, phenylcarbene, and pyridylcarbenes. Rearrangements to cyanocyclopentadiene and fulvenallene. J. Am. Chem. Soc. 136, 15203–15214 (2014).
Article CAS PubMed Google Scholar
Gomberg, M. An instance of trivalent carbon: triphenylmethyl. J. Am. Chem. Soc. 22, 757–771 (1900).
Zard, S. Z. Recent progress in the generation and use of nitrogen-centred radicals. Chem. Soc. Rev. 37, 1603–1618 (2008).
Article CAS PubMed Google Scholar
Hirai, K., Itoh, T. & Tomioka, H. Persistent triplet carbenes. Chem. Rev. 109, 3275–3332 (2009).
Article CAS PubMed Google Scholar
Wentrup, C. Carbenes and nitrenes: recent developments in fundamental chemistry. Angew. Chem. Int. Ed. 57, 11508–11521 (2018).
Soleilhavoup, M. & Bertrand, G. Stable carbenes, nitrenes, phosphinidenes, and borylenes: past and future. Chem 6, 1275–1282 (2020).
He, M., Hu, C., Wei, R., Wang, X.-F. & Liu, L. L. Recent advances in the chemistry of isolable carbene analogues with group 13–15 elements. Chem. Soc. Rev. 53, 3896–3951 (2024).
Article CAS PubMed Google Scholar
Igau, A., Grutzmacher, H., Baceiredo, A. & Bertrand, G. Analogous α,α′-bis-carbenoid triply bonded species: synthesis of a stable λ3-phosphinocarbene-λ5-phosphaacetylene. J. Am. Chem. Soc. 110, 6463–6466 (1988).
Arduengo, A. J., Harlow, R. L. & Kline, M. A stable crystalline carbene. J. Am. Chem. Soc. 113, 361–363 (1991).
Bourissou, D., Guerret, O., Gabbaï, F. P. & Bertrand, G. Stable carbenes. Chem. Rev. 100, 39–92 (2000).
Article CAS PubMed Google Scholar
Sau, S. C., Hota, P. K., Mandal, S. K., Soleilhavoup, M. & Bertrand, G. Stable abnormal N-heterocyclic carbenes and their applications. Chem. Soc. Rev. 49, 1233–1252 (2020).
Article CAS PubMed Google Scholar
Bellotti, P., Koy, M., Hopkinson, M. N. & Glorius, F. Recent advances in the chemistry and applications of N-heterocyclic carbenes. Nat. Rev. Chem. 5, 711–725 (2021).
Article CAS PubMed Google Scholar
Badiei, Y. M., Krishnaswamy, A., Melzer, M. M. & Warren, T. H. Transient terminal Cu–nitrene intermediates from discrete dicopper nitrenes. J. Am. Chem. Soc. 128, 15056–15057 (2006).
Article CAS PubMed Google Scholar
Carsch, K. M. et al. Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination. Science 365, 1138 (2019).
Article CAS PubMed PubMed Central Google Scholar
Das, A. et al. In crystallo snapshots of Rh2-catalyzed C–H amination. J. Am. Chem. Soc. 142, 19862–19867 (2020).
Article CAS PubMed Google Scholar
Grünwald, A. et al. Palladium terminal imido complexes with nitrene character. J. Am. Chem. Soc. 144, 8897–8901 (2022).
Jung, H. et al. Mechanistic snapshots of rhodium-catalyzed acylnitrene transfer reactions. Science 381, 525–532 (2023).
Article CAS PubMed Google Scholar
Keilwerth, M. et al. From divalent to pentavalent iron imido complexes and an Fe(V) nitride via N–C bond cleavage. J. Am. Chem. Soc. 145, 873–887 (2023).
Article CAS PubMed Google Scholar
Mao, W. et al. Synthesis and reactivity of a cobalt-supported singlet nitrene. J. Am. Chem. Soc. 145, 13650–13662 (2023).
Article CAS PubMed Google Scholar
Dielmann, F. et al. A crystalline singlet phosphinonitrene: a nitrogen atom–transfer agent. Science 337, 1526–1528 (2012).
Article CAS PubMed Google Scholar
Sun, J. et al. A platinum(II) metallonitrene with a triplet ground state. Nat. Chem. 12, 1054–1059 (2020).
Article CAS PubMed Google Scholar
Schmidt-Räntsch, T. et al. Nitrogen atom transfer catalysis by metallonitrene C−H insertion: photocatalytic amidation of aldehydes. Angew. Chem. Int. Ed. 61, e202115626 (2022).
Domenianni, L. I. et al. Photoinduced metallonitrene formation by N2 elimination from azide diradical ligands. Angew. Chem. Int. Ed. 62, e202309618 (2023).
Matsuo, T. et al. Synthesis and structures of a series of bulky ‘Rind-Br’ based on a rigid fused-ring s-hydrindacene skeleton. Bull. Chem. Soc. Jpn. 84, 1178–1191 (2011).
Olaru, M., Mebs, S. & Beckmann, J. Cationic carbene analogues: donor-free phosphenium and arsenium ions. Angew. Chem. Int. Ed. 60, 19133–19138 (2021).
He, Y., Dai, C., Wang, D., Zhu, J. & Tan, G. Phosphine-stabilized germylidenylpnictinidenes as synthetic equivalents of heavier nitrile and isocyanide in cycloaddition reactions with alkynes. J. Am. Chem. Soc. 144, 5126–5135 (2022).
Article CAS PubMed Google Scholar
Janssen, M., Mebs, S. & Beckmann, J. Kinetically stabilized diarylpnictogenium ions. ChemPlusChem 88, e202200429 (2023).
Article CAS PubMed Google Scholar
Pang, Y. et al. Synthesis and isolation of a triplet bismuthinidene with a quenched magnetic response. Science 380, 1043–1048 (2023).
Article CAS PubMed Google Scholar
Wang, D. et al. Monosubstituted doublet Sn(I) radical featuring substantial unquenched orbital angular momentum. J. Am. Chem. Soc. 145, 6914–6920 (2023).
Article CAS PubMed Google Scholar
Wang, D. et al. An isolable germylyne radical with a one-coordinate germanium atom. Nat. Chem. 15, 200–205 (2023).
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