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Karbeny N-heterocykliczne : synteza i zastosowanie

Malinowska M., Hryniewicka A.

Wiadomości Chemiczne

2015

[Z] 69, 3-4

227--253

N-Heterocyclic carbenes (NHCs) are powerful tools in organic chemistry, with numerous applications in academic and industrial laboratories. They are usually defined as singlet carbenes, in which the divalent carbonic centre is connected directly to at least one nitrogen atom in the heterocycle [1]. They have played an important role in organic chemistry ever since the first evidence of their existence. The isolation of stable, free 1,3‑diadamantylimidazol-2-ylidene (IAd, Fig. 1) by Arduengo et al. in 1991 was a milestone in the chemistry of carbenes [2]. From the beginnings as academic curiosities, N‑heterocyclic carbenes today are very useful compounds in a variety of organic transformations (Fig. 13). NHCs are neutral σ-donors, which form very strong bonds with the majority of transition metals (stronger than phosphines). These compounds are easy-to-make ligands with great potential in homogeneous catalysis (mainly ruthenium and palladium complexes) for large number of reactions, including the coupling reactions (Heck, Negishi, Stille, Suzuki or Sonogashira reactions) and olefin metathesis [3]. Moreover, they are very useful as organocatalysts used in the benzoin condensation, the Stetter reaction and ring-opening polymerization (ROP) or transesterification [4]. In this review, we aim to give an overview of the properties and applications of NHCs, which we expect will be a useful introduction for chemists interested in studying and applying these important compounds. The first part of this review is devoted to the main synthetic routes to NHCs, their properties and reactivity. In the second part we describe the metal complexes with NHCs as homogeneous catalysts and their applications in various types of reactions. At the end of this part of the paper the use of NHCs as organocatalysts is presented.