Frustrated Lewis Pairs II by Gerhard Erker & Douglas W. Stephan

Author:Gerhard Erker & Douglas W. Stephan
Language: eng
Format: epub
Publisher: Springer Berlin Heidelberg, Berlin, Heidelberg

Keywords

CarbeneYlideAlleneNQO1EnamineDisulfides

1 Introduction

The extension of the FLP concept to include currently unexplored partners is desirable as it may lead to the discovery of a range of interesting new applications. If we focus our attention on carbon-based FLPs it seems logical to divide them into three different groups depending on the nature of the base and acid involved: (1) FLPs in which only the base is carbogenic, (2) FLPs containing a carbon-based acid, and (3) FLPs in which both partners are carbon-based. Probably the most obvious carbon-based bases for this chemistry are N-heterocyclic carbenes (NHCs) due to their strong basicity combined with the easy modulation of their stereoelectronic properties. The advances in this particular field are reviewed in the earlier chapter by M. Tamm. However, other carbon-based bases such as enamines or ylides have also been applied in this area and are depicted in Sect. 2 of this chapter. Studies involving FLPs in which only the acidic partner has a carbogenic nature are quite scarce, the work of Stephan with tritylium cations probably being the most prominent example. These results are shown in Sect. 3. Finally, the last section of this chapter will be devoted to those systems in which both partners are carbon-based. Up to now these FLPs are constituted by a bulky NHC acting as a base in concurrence with an electron poor allene that behaves as a carbon-based neutral surrogate of B(C6F5)3.

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