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01-14-2010
VIP: Steering the Surprisingly Modular π-Acceptor Properties of N-Heterocyclic Carbenes: Implications for Gold Catalysis

Manuel Alcarazo, Timon Stork, Anakuthil Anoop, Walter Thiel, and Alois Fürstner*

Whereas the excellent σ-donor qualities of N-heterocyclic carbenes (NHCs) are extensively used for homogeneous catalysis, the π-acceptor properties of such ancillary ligands are often considered weak or even negligible. It is now shown by three mechanistically distinct gold-catalyzed reactions that the acceptor properties of NHCs can be up-regulated to the extent where they start dictating the observed reactivity. This is the case in cyclophanic NHCs, in triazolylidenes, as well as in the recently disclosed class of amino–ylide carbenes (AYCs). DFT calculations and electrochemical data support this notion.

Eingegangen am 21. Dezember 2009, online veröffentlicht am 04. März 2010, DOI: 10.1002/ange.200907194.

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Von Angewandten-Autoren:
D. Astruc (Hrsg): Modern Arene Chemistry



 

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