Chiral [Iminophosphoranyl]ferrocenes: Synthesis, Coordination Chemistry, and Catalytic Application 


Vol. 26,  No. 9, pp. 1359-1365, Sep.  2005
10.5012/bkcs.2005.26.9.1359


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  Abstract

A series of new chiral [iminophosphoranyl]ferrocenes, {η5-54-(PP2=N-2,6-2-63)}Fe{η5-53-1-PPh2-2-CH(Me)NM2} (1: R = Me, iPr), {η5-54-(PP2=N-2,6-21-63)}Fe{η5-53-1-(PP2=N-2,6-2-63)-2-CH(Me)R2} (2: R1 = Me, Pr; R2 = NM2, OMe), and (η5-55)Fe{η5-54-1-P2-2-CH(Me)N=PP3} (3:R = Ph, 611) have been prepared from the reaction of [1,1'-diphenylphosphino-2-(N,N-dimethylamino) ethyl]ferrocene with arylazides (1 & 2) and the reaction of phosphine dichlorides (3PC2) with [1,1'- diphenylphosphino-2-aminoethyl]ferrocene (3), respectively. They form palladium complexes of the type [Pd(35)(L)]B4 (4-6: L = 1-3), where the ligand (L) adopts an η2-N,N (2) or η2-P,N (3) as expected. In the case of 1, a potential terdentate, an η2-P,N mode is realized with the exclusion of the ?P=NAr group from the coordination sphere. Complexes 4-6 were employed as catalysts for allylic alkylation of 1,3-diphenylallyl acetate leading to an almost stoichiometric product yield with modest enantiomeric excess (up to 74% ee). Rh(I)-complexes incorporating 1-3 were also prepared in situ for allylic alkylation of cinnamyl acetate as a probe for both regio- and enantioselectivities of the reaction. The reaction exhibited high regiocontrol in favor of a linear achiral isomer regardless of the ligand employed.

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  Cite this article

[IEEE Style]

T. T. Co, S. C. Shim, C. S. Cho, D. Kim, T. Kim, "Chiral [Iminophosphoranyl]ferrocenes: Synthesis, Coordination Chemistry, and Catalytic Application," Bulletin of the Korean Chemical Society, vol. 26, no. 9, pp. 1359-1365, 2005. DOI: 10.5012/bkcs.2005.26.9.1359.

[ACM Style]

Thanh Thien Co, Sang Chul Shim, Chan Sik Cho, Dong-Uk Kim, and Tae-Jeong Kim. 2005. Chiral [Iminophosphoranyl]ferrocenes: Synthesis, Coordination Chemistry, and Catalytic Application. Bulletin of the Korean Chemical Society, 26, 9, (2005), 1359-1365. DOI: 10.5012/bkcs.2005.26.9.1359.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949