Abstract
The activation of the P═C bond of phosphaalkenes with N-heterocyclic carbenes (NHCs) offers a convenient means to introduce new functionality at the 4-position of an NHC. Treatment of MesP═CRR′ (2a: R = R′ = Ph; 2b: R = Ph, R′ = 2-C5H4N; 2c: R = R′ = 4-C6H4F) with 1,3-dimesitylimidazol-2-ylidene [:C(NMesCH)2, IMes, Mes = 2,4,6-Me3C6H2] affords 4-phosphino-2-carbenes :C(NMes)2CHC(PMesCHRR′)NMes [1a: R = R′ = Ph; 1b: R = Ph, R′ = 2-C5H4N; 1c: R = R′ = 4-C6H4F]. Significantly, these functional NHCs retain the parent carbene functionality and, in addition, contain a phosphine moiety. The preparation and spectroscopic characterization of the complexes [(1a)M(cod)Cl] (4) and cis-[(1a)M(CO)2Cl] (5) (M = Ir, Rh) are reported. The average CO stretching frequencies (νCOav) for 5M=Ir, 5M=Rh, and authentic samples of cis-[(IMes)M(CO)2Cl] (M = Ir, Rh) are presented as a means to evaluate the donor properties of 4-phosphino-2-carbene 1a. The average CO stretching frequency is lower energy for 5M=Ir than for cis-[(IMes...
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