Synthesis of Alkyl and Fluoroalkyl
Chains Containing Thioether-Phosphines

Angela M. López-Vinasco; Marlene Bruce; Paola González-Aguirre; Alonso Rosas-Hernández; Carlos Amador-Bedolla; Erika Martin

doi:10.1055/s-0030-1258309

PAPER

Synthesis of Alkyl and Fluoroalkyl Chains Containing Thioether-Phosphines

Angela M. López-Vinasco^a, Marlene Bruce^a, Paola González-Aguirre^a, Alonso Rosas-Hernández^a, Carlos Amador-Bedolla^b, Erika Martin*^a
^a Depto. de Química Inorgánica, Facultad de Química, Universidad Nacional Autónoma de México, Av. Universidad 3000, 04510 México D.F., México
Fax: +52(55)56223720; e-Mail: erikam@unam.mx;
^b Depto. de Física y Química Teórica, Facultad de Química, Universidad Nacional Autónoma de México, Av. Universidad 3000, 04510 México D.F., México

Abstract

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Abstract

We prepared new thioether-arylphosphines bearing alkyl and fluoroalkyl chains at the sulfur atom in order to use them in metal-catalyzed reactions in new reaction media, such as a fluorous biphasic system. The characterization of the new compounds is discussed and the partition coefficients in the biphasic system perfluoromethylcyclohexane-cyclohexane were determined. Fluorous thioether-phosphines reacted with [Rh(acac)(CO)₂] under fluorous biphasic conditions to produce rhodium species retained in the fluorous phase with ≤2.32 ppm of rhodium loss in the organic phase. The effect of S-ponytails on the coordination properties of the new phosphines and their relation with ^³¹P NMR chemical shifts were supported by DFT calculations.

Key words

P,S-ligands - fluoroalkyl halides - thioether compounds - fluorinated arylphosphines - biphase systems

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