A Mechanistically and Operationally Simple Route to Metal–N‐Heterocyclic Carbene (NHC) Complexes

We have been puzzled by the involvement of weak organic and inorganic bases in the synthesis of metal–N‐heterocyclic carbene (NHC) complexes. Such bases are insufficiently strong to permit the presumed required deprotonation of the azolium salt (the carbene precursor) prior to metal binding. Experim...

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Bibliographic Details
Published in:Chemistry : a European journal 2020-04, Vol.26 (20), p.4515-4519
Main Authors: Tzouras, Nikolaos V., Nahra, Fady, Falivene, Laura, Cavallo, Luigi, Saab, Marina, Van Hecke, Kristof, Collado, Alba, Collett, Christopher J., Smith, Andrew D., Cazin, Catherine S. J., Nolan, Steven P.
Format: Article
Language:English
Subjects:
Chemistry
complexes
Computer applications
mechanism
Metals
N-heterocyclic carbenes
synthesis
weak bases
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Summary:We have been puzzled by the involvement of weak organic and inorganic bases in the synthesis of metal–N‐heterocyclic carbene (NHC) complexes. Such bases are insufficiently strong to permit the presumed required deprotonation of the azolium salt (the carbene precursor) prior to metal binding. Experimental and computational studies provide support for a base‐assisted concerted process that does not require free NHC formation. The synthetic protocol was found applicable to a number of transition‐metal‐ and main‐group‐centered NHC compounds and could become the synthetic route of choice to form M–NHC bonds. No free carbene required: Computational and experimental investigations of a weak base‐assisted synthetic route leading to metal–NHC complexes suggest a concerted mechanism is at play. The method is exemplified with metal and nonmetal centers and establishes its synthetic utility.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202000564