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Synthesis 2010(23): 4101-4106  
DOI: 10.1055/s-0030-1258309
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Alkyl and Fluoroalkyl Chains Containing Thioether-Phosphines

Angela M. López-Vinascoa, Marlene Brucea, Paola González-Aguirrea, Alonso Rosas-Hernándeza, Carlos Amador-Bedollab, 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
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Publication History

Received 16 June 2010
Publication Date:
22 October 2010 (online)

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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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